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1069-66-5

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1069-66-5 Usage

Description

Sodium Valproate (1069-66-5) is a histone deacetylase inhibitor (IC50 = 400μM).1 Demonstrates neuroprotective, anticancer, and anti-inflammatory activity.2? Inhibits Aβ production, reduced neuritic plaque formation, and improved memory deficits in Alzheimer’s mouse models.3? Improves stem cell reprogramming efficiency and enables efficient induction of pluripotency without introduction of the oncogene c-Myc.4 Clinically useful anticonvulsant.

Chemical Properties

White Solid

Originator

Anticon,Generics-UK,UK

Uses

Different sources of media describe the Uses of 1069-66-5 differently. You can refer to the following data:
1. Antiepileptic; increases levels of GABA in the brain
2. antibacterial
3. Anticonvulsant

Definition

ChEBI: The sodium salt of valproic acid.

Manufacturing Process

(a) Di-n-propyl cyanacetic acid First of all, a sodium n-propylate solution was prepared from 7.42 g (0.322 mol) of sodium and 180 ml of anhydrous n-propanol, by heating with gentle reflux until complete dissolution of the sodium. Into a 500 ml spherical flask, equipped with a dropping funnel, a mechanical stirrer, a thermometer and a condenser, above which was disposed a calcium chloride trap, were introduced 16.95 g (0.141 mol) of ethyl cyanacetate and 40.69 g (0.33 mol) of n-propyl bromide. This mixture was heated to 45°C and then there was added thereto, slowly and while stirring, the previously prepared solution of sodium n-propylate, keeping the temperature of the reaction medium at 50°-55°C by gentle external cooling.With the completion of the operation of introduction, the mixture was brought to reflux temperature in 30 minutes and kept at this temperature for 3 hours. The n-propanol was then distilled and the distillation stopped when the temperature of the residual mass had reached 115°C. The crude ester obtained in this way was then treated with a solution of 7.5 g of flaked sodium hydroxide in 67.5 ml of water. The mixture was introduced into a 250 ml spherical flask, equipped with a condenser, and then the reaction medium was slowly brought to 60°-70°C. This temperature was maintained for 3 hours, whereafter the mixture was cooled to about 50°C and the ethanol which had formed and the residue of n-propanol were eliminated under a pressure of 70 mm Hg. The solution thus obtained was cooled to 20°C and acidified, while stirring, by addition of 26.25 g of 36% hydrochloric acid. During this operation, the temperature of the reaction medium was kept below 40°C by cooling. Stirring was continued for 30 minutes, whereafter the mixture was left standing for 30 minutes. The oily layer of di-n-propyl cyanacetic acid was decanted and the aqueous phase extracted with 35 ml of toluene. The extract in toluene was then added to the decanted di-n-propyl cyanacetic acid, whereafter the solution in toluene was washed, in a separation funnel, with a solution of 1.5 g of sodium chloride in 14 ml of water. The toluenic phase was decanted and the toluene distilled under atmospheric pressure. Using this procedure, 25 g of crude di-n-propyl cyanacetic acid were obtained. (b) Di-n-propyl acetonitrile Into a 100 ml spherical flask fitted with a thermometer and a condenser were introduced 25 g of crude di-n-propyl cyanacetic acid obtained by the method previously described, and the mixture was heated on an oil bath. Decarboxylation commenced at a temperature in the region of 140°C. The mixture was refluxed at about 160°C and at 190°C for 2 hours. This temperature was maintained until the release of gas was completed, this taking 2 hours. The di-n-propyl acetonitrile thus formed was then slowly distilled and the fraction passing over between 165°C and 175°C was collected. A second distillation was then carried out. Using this procedure, 14.7 g of di-n-propyl acetonitrile were collected. Boiling point: 170°C. Yield: 83%, relatively to the ethyl cyanacetate used. Di-n-propyl acetonitrile may be saponifyed with equal molecular quantity of NaOH to give the desired valproic acid (valproate). After that it may be converted into the sodium salt with help of equivalent NaOH to give the valproate sodium.

Brand name

Depacon (Abbott).

Therapeutic Function

Anticonvulsant, Antiepileptic

General Description

A cell-permeable, short-chained fatty acid that inhibits histone deacetylase activity (IC50 = 400 μM for HDAC1). Induces differentiation and inhibits proliferation of cell lines derived from human malignant gliomas. At therapeutic levels (350 μM-1.04 mM), causes inositol depletion, inhibits both GSK-3α and -3β, activates the ERK pathway, and produces neurotropic effects. Has been used as an anti-epileptic agent. Also reported to stimulate peroxisome proliferator-activated receptor (PPAR) activity. Displays a potent teratogenic activity in humans and rodent models.

Biological Activity

Histone deacetylase inhibitor (IC 50 = 400 μ M) that exhibits anticancer, anti-inflammatory and neuroprotective effects. Displays anticonvulsive activity via an increase in GABA levels and decreases A β production in animal models of Alzheimer's disease. Also attenuates NMDA-mediated excitation, blocks voltage-gated Na + channels and modulates firing of neurons. Enables induction of pluripotent stem cells from somatic cells by Oct4 and Sox2.

Biochem/physiol Actions

Cell permeable: yes

Clinical Use

All forms of epilepsy Migraine prophylaxis (unlicensed)

in vitro

vpa showed to have cellular neuroprotective properties. in cultured neurons, vpa protected from thapsigargin-induced endoplasmic reticulum stress, glutamate-induced excitotoxicity, as well as lipopolysaccharide (lps)-induced dopaminergic neuronal death. in midbrain neuron-glia cultures, vpa was also shown to inhibit lps-induced, microglia-mediated inflammation [1].

in vivo

post-pmcao injections with vpa could decrease the brain infarct volume. postinsult treatment with vpa also reduced the number of microglia, suppressed microglial activation, and inhibited other inflammatory markers in the ischemic brain. the reduction in acetylated histone h3 was prevented by treatment with vpa. moreover, vpa superinduced heat-shock protein 70 and blocked pmcao-induced down-regulation of cyclooxygenase-2. the sensory, motor, and reflex performance of pmcao rats was improved by vpa treatment [1].

Drug interactions

Potentially hazardous interactions with other drugs Antibacterials: metabolism possibly inhibited by erythromycin; avoid with pivmecillinam; concentration reduced by carbapenems - avoid. Antidepressants: antagonise anticonvulsant effect; avoid with St John’s wort. Antiepileptics: concentration reduced by carbamazepine; concentration of active carbamazepine metabolite increased; increased concentration of lamotrigine, phenobarbital, rufinamide and possibly ethosuximide; sometimes reduces concentration of active metabolite of oxcarbazepine; alters phenytoin concentration; phenytoin and phenobarbital reduce valproate concentration; hyperammonaemia and CNS toxicity with topiramate. Antimalarials: mefloquine antagonises anticonvulsant effect. Antipsychotics: antagonise anticonvulsant effect; increased neutropenia with olanzapine; possibly increases or decreases concentration of clozapine; possibly increases quetiapine concentration. Ciclosporin: variable ciclosporin blood level response. Orlistat: possibly increased risk of convulsions. Sodium oxybate: concentration of sodium oxybate increased. Ulcer-healing drugs: metabolism inhibited by cimetidine, increased concentration.

IC 50

0.4 mm

Metabolism

Valproic acid is extensively metabolised in the liver, a large part by glucuronidation (up to 60%) and the rest by a variety of complex pathways (up to 45%). It is excreted in the urine almost entirely in the form of its metabolites; small amounts are excreted in faeces and expired air.

References

1) Phiel et al. (2001), Histone deacetylase is a direct target of valproic acid, a potent anticonvulsant, mood stabilizer, and teratogen; J. Biol. Chem. 276 36734 2) Kim et al. (2007), Histone deacetylase inhibitors exhibit anti-inflammatory and neuroprotective effects in a rat permanent ischemic model of stroke: multiple mechanisms of action; J. Pharmacol. Exp. Ther. 321 892 3) Qing et al. (2008), Valproic acid inhibits Abeta production, neuritic plaque formation, and behavioral deficits in Alzheimer’s mouse models; J. Exp. Med. 205 2781 4) Hangfu et al. (2008), Induction of pluripotent stem cells by defined factors is greatly improved by small molecule compounds; Nat. Biotechnol. 26 795

Check Digit Verification of cas no

The CAS Registry Mumber 1069-66-5 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 1,0,6 and 9 respectively; the second part has 2 digits, 6 and 6 respectively.
Calculate Digit Verification of CAS Registry Number 1069-66:
(6*1)+(5*0)+(4*6)+(3*9)+(2*6)+(1*6)=75
75 % 10 = 5
So 1069-66-5 is a valid CAS Registry Number.
InChI:InChI=1/C8H16O2.Na/c1-3-5-7(6-4-2)8(9)10;/h7H,3-6H2,1-2H3,(H,9,10);/q;+1/p-1

1069-66-5 Well-known Company Product Price

  • Brand
  • (Code)Product description
  • CAS number
  • Packaging
  • Price
  • Detail
  • TCI America

  • (S0894)  Sodium 2-Propylvalerate  >98.0%(T)

  • 1069-66-5

  • 25g

  • 490.00CNY

  • Detail
  • TCI America

  • (S0894)  Sodium 2-Propylvalerate  >98.0%(T)

  • 1069-66-5

  • 100g

  • 1,450.00CNY

  • Detail
  • Sigma-Aldrich

  • (S0930000)  Sodium valproate  European Pharmacopoeia (EP) Reference Standard

  • 1069-66-5

  • S0930000

  • 1,880.19CNY

  • Detail
  • Sigma

  • (P4543)  Valproicacidsodiumsalt  ≥98%

  • 1069-66-5

  • P4543-10G

  • 458.64CNY

  • Detail
  • Sigma

  • (P4543)  Valproicacidsodiumsalt  ≥98%

  • 1069-66-5

  • P4543-25G

  • 766.35CNY

  • Detail
  • Sigma

  • (P4543)  Valproicacidsodiumsalt  ≥98%

  • 1069-66-5

  • P4543-100G

  • 2,315.43CNY

  • Detail

1069-66-5SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 17, 2017

Revision Date: Aug 17, 2017

1.Identification

1.1 GHS Product identifier

Product name sodium valproate

1.2 Other means of identification

Product number -
Other names sodium,2-propylpentanoate

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:1069-66-5 SDS

1069-66-5Synthetic route

valproic acid
99-66-1

valproic acid

sodium valproate
1069-66-5

sodium valproate

Conditions
ConditionsYield
With sodium hydroxide In water Product distribution / selectivity;100%
With sodium hydroxide In water at 20℃;100%
With sodium hydroxide In toluene97.7%
With sodium hydroxide
ethyl 2-propylpentanoate
17022-31-0

ethyl 2-propylpentanoate

sodium valproate
1069-66-5

sodium valproate

Conditions
ConditionsYield
With methanol; sodium hydroxide for 9h; Time; Reflux; Large scale;87.2%
propyl bromide
106-94-5

propyl bromide

diethyl malonate
105-53-3

diethyl malonate

sodium valproate
1069-66-5

sodium valproate

Conditions
ConditionsYield
Stage #1: propyl bromide; diethyl malonate With sodium ethanolate In ethanol at 50℃; for 2h;
Stage #2: With sodium hydroxide In water at 60℃; for 3h;
Stage #3: at 110℃;
copper(II) choride dihydrate

copper(II) choride dihydrate

sodium valproate
1069-66-5

sodium valproate

Cu2(valproate)4
108558-25-4

Cu2(valproate)4

Conditions
ConditionsYield
In water for 24h;99%
[ruthenium(II)(η6-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]2
52462-29-0

[ruthenium(II)(η6-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]2

sodium valproate
1069-66-5

sodium valproate

[RuCl(κ2O-vpCO2)(η6-p-cymene)]

[RuCl(κ2O-vpCO2)(η6-p-cymene)]

Conditions
ConditionsYield
In methanol at 20℃; for 2h;96%
valproic acid
99-66-1

valproic acid

sodium valproate
1069-66-5

sodium valproate

divalproex sodium

divalproex sodium

Conditions
ConditionsYield
In acetonitrile Product distribution / selectivity; Heating / reflux;93.75%
In acetone at 50℃; for 0.166667h;
1,1'-(2,2'-dimethoxy-[1,1'-binaphthalene]-6,6'-diyl)bis(2-bromoethanone)

1,1'-(2,2'-dimethoxy-[1,1'-binaphthalene]-6,6'-diyl)bis(2-bromoethanone)

sodium valproate
1069-66-5

sodium valproate

(2,2'-dimethoxy-[1,1'-binaphthalene]-6,6'-diyl)bis(2-oxoethane-2,1-diyl) bis(2-propylpentanoate)

(2,2'-dimethoxy-[1,1'-binaphthalene]-6,6'-diyl)bis(2-oxoethane-2,1-diyl) bis(2-propylpentanoate)

Conditions
ConditionsYield
In acetonitrile at 20℃; for 4h;92%
sodium valproate
1069-66-5

sodium valproate

zinc(II) chloride
7646-85-7

zinc(II) chloride

zinc(II) valproate

zinc(II) valproate

Conditions
ConditionsYield
In water88%
sodium valproate
1069-66-5

sodium valproate

zinc(II) chloride
7646-85-7

zinc(II) chloride

[Zn2(valproate)4]

[Zn2(valproate)4]

Conditions
ConditionsYield
In water at 20℃;88%
sodium valproate
1069-66-5

sodium valproate

zinc(II) chloride
7646-85-7

zinc(II) chloride

[tetrakis-μ-2-propylpentanoatezinc(II)]

[tetrakis-μ-2-propylpentanoatezinc(II)]

Conditions
ConditionsYield
In water at 20℃; for 24h;88%
In water at 20℃; for 1h;
1-(4-chlorophenyl)-3-methyltriazene
20667-72-5, 20667-73-6, 40843-82-1

1-(4-chlorophenyl)-3-methyltriazene

sodium valproate
1069-66-5

sodium valproate

1-(4-chlorophenyl)-3-methyl-3-[2-(propyl)pentanoyl]triazene

1-(4-chlorophenyl)-3-methyl-3-[2-(propyl)pentanoyl]triazene

Conditions
ConditionsYield
Stage #1: sodium valproate With benzotriazol-1-ol In tetrahydrofuran at 20℃; for 0.25h;
Stage #2: With 1,1'-carbonyldiimidazole In tetrahydrofuran for 0.75h; Inert atmosphere;
Stage #3: 1-(4-chlorophenyl)-3-methyltriazene With sodium hydride; triethylamine In tetrahydrofuran; dichloromethane; mineral oil for 48h; Inert atmosphere;
87.2%
cobalt(II) chloride hexahydrate

cobalt(II) chloride hexahydrate

sodium valproate
1069-66-5

sodium valproate

[Co2(valporate)4]

[Co2(valporate)4]

Conditions
ConditionsYield
In water at 20℃;86.5%
cobalt(II) chloride hexahydrate

cobalt(II) chloride hexahydrate

sodium valproate
1069-66-5

sodium valproate

[Co2(valp)4]

[Co2(valp)4]

Conditions
ConditionsYield
In water at 20℃;86.5%
1H-imidazole
288-32-4

1H-imidazole

cadmium(II) chloride dihydrate

cadmium(II) chloride dihydrate

sodium valproate
1069-66-5

sodium valproate

Cd(valproate)2(imidazole)2

Cd(valproate)2(imidazole)2

Conditions
ConditionsYield
In methanol at 20℃; for 2h;86%
1,10-Phenanthroline
66-71-7

1,10-Phenanthroline

cadmium(II) chloride dihydrate

cadmium(II) chloride dihydrate

sodium valproate
1069-66-5

sodium valproate

Cd(valproate)2(1,10-phenanthroline)H2O

Cd(valproate)2(1,10-phenanthroline)H2O

Conditions
ConditionsYield
In methanol at 20℃; for 2h;83%
1,1'-(2,2'-dihydroxy-[1,1'-binaphthalene]-6,6'-diyl)bis(2-bromoethanone)

1,1'-(2,2'-dihydroxy-[1,1'-binaphthalene]-6,6'-diyl)bis(2-bromoethanone)

sodium valproate
1069-66-5

sodium valproate

Conditions
ConditionsYield
In acetonitrile at 20℃; for 4h;83%
(8S,9S,10R,13S,14S,17S)-17-((E)-1-(hydroxyimino)ethyl)-10,13-dimethyl-6,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3(2H)one

(8S,9S,10R,13S,14S,17S)-17-((E)-1-(hydroxyimino)ethyl)-10,13-dimethyl-6,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3(2H)one

sodium valproate
1069-66-5

sodium valproate

(8S,9S,10R,13S,14S,17S)-10,13-dimethyl-17-((E)-1-(2-propylpentanoyloxyimino)ethyl)-6,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3(2H)-one
1364711-92-1

(8S,9S,10R,13S,14S,17S)-10,13-dimethyl-17-((E)-1-(2-propylpentanoyloxyimino)ethyl)-6,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3(2H)-one

Conditions
ConditionsYield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In dichloromethane at 0 - 20℃; for 16h; Inert atmosphere;79%
(8S,9S,10R,13S,14S,17S)-17-((E)-1-(hydroxyimino)ethyl)-10,13-dimethyl-6,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3(2H)-one
1364709-15-8

(8S,9S,10R,13S,14S,17S)-17-((E)-1-(hydroxyimino)ethyl)-10,13-dimethyl-6,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3(2H)-one

sodium valproate
1069-66-5

sodium valproate

(8S,9S,10R,13S,14S,17S)-10,13-dimethyl-17-((E)-1-(2-propylpentanoyloxyimino)ethyl)-6,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3(2H)-one
1364711-92-1

(8S,9S,10R,13S,14S,17S)-10,13-dimethyl-17-((E)-1-(2-propylpentanoyloxyimino)ethyl)-6,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3(2H)-one

Conditions
ConditionsYield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 16h; Inert atmosphere;79%
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 16h; Inert atmosphere;79%
cetylpyridinium chloride
123-03-5

cetylpyridinium chloride

sodium valproate
1069-66-5

sodium valproate

hexadecylpyridinium valproic acid
934544-54-4

hexadecylpyridinium valproic acid

Conditions
ConditionsYield
In water at 20℃; for 1h;77.14%
1,10-Phenanthroline
66-71-7

1,10-Phenanthroline

cobalt(II) chloride hexahydrate

cobalt(II) chloride hexahydrate

sodium valproate
1069-66-5

sodium valproate

Co(valproate)2(1,10-phenanthroline)H2O

Co(valproate)2(1,10-phenanthroline)H2O

Conditions
ConditionsYield
In methanol at 20℃; for 2h;76%
1H-imidazole
288-32-4

1H-imidazole

cobalt(II) chloride hexahydrate

cobalt(II) chloride hexahydrate

sodium valproate
1069-66-5

sodium valproate

Co(valproate)2(imidazole)2

Co(valproate)2(imidazole)2

Conditions
ConditionsYield
In methanol at 20℃; for 2h;76%
1,10-Phenanthroline
66-71-7

1,10-Phenanthroline

manganese (II) acetate tetrahydrate
6156-78-1

manganese (II) acetate tetrahydrate

sodium valproate
1069-66-5

sodium valproate

Mn(valproate)2(1,10-phenanthroline)H2O

Mn(valproate)2(1,10-phenanthroline)H2O

Conditions
ConditionsYield
In methanol at 20℃; for 2h;76%
1H-imidazole
288-32-4

1H-imidazole

palladium diacetate
3375-31-3

palladium diacetate

sodium valproate
1069-66-5

sodium valproate

[Pd(valproate)2(imidazole)2]

[Pd(valproate)2(imidazole)2]

Conditions
ConditionsYield
In ethanol at 20℃; for 4h;75%
ethanol
64-17-5

ethanol

diphenyltin(IV) dichloride
1135-99-5

diphenyltin(IV) dichloride

sodium valproate
1069-66-5

sodium valproate

6C8H15O2(1-)*6Sn(4+)*6C6H5(1-)*6O(2-)

6C8H15O2(1-)*6Sn(4+)*6C6H5(1-)*6O(2-)

Conditions
ConditionsYield
for 5h; Reflux;72%
1,4-pyrazine
290-37-9

1,4-pyrazine

palladium diacetate
3375-31-3

palladium diacetate

sodium valproate
1069-66-5

sodium valproate

[Pd(valproate)2(pyrazine)2]

[Pd(valproate)2(pyrazine)2]

Conditions
ConditionsYield
In ethanol at 20℃; for 4h;72%
sodium valproate
1069-66-5

sodium valproate

triphenyltin chloride
639-58-7

triphenyltin chloride

Ph3Sn(valproate)

Ph3Sn(valproate)

Conditions
ConditionsYield
In ethanol for 5h; Reflux;67%
trimethyltin(IV)chloride
1066-45-1

trimethyltin(IV)chloride

sodium valproate
1069-66-5

sodium valproate

Me3Sn(valproate)

Me3Sn(valproate)

Conditions
ConditionsYield
In ethanol for 5h; Reflux;62%
tributyltin chloride
1461-22-9

tributyltin chloride

sodium valproate
1069-66-5

sodium valproate

Bu3Sn(valproate)

Bu3Sn(valproate)

Conditions
ConditionsYield
In ethanol for 5h; Reflux;58%
sodium valproate
1069-66-5

sodium valproate

1-(4-carbamoylphenyl)-3-methyltriazene

1-(4-carbamoylphenyl)-3-methyltriazene

1-(4-carbamoylphenyl)-3-methyl-3-[2-(propyl)pentanoyl]triazene

1-(4-carbamoylphenyl)-3-methyl-3-[2-(propyl)pentanoyl]triazene

Conditions
ConditionsYield
Stage #1: sodium valproate With benzotriazol-1-ol In tetrahydrofuran at 20℃; for 0.25h;
Stage #2: With 1,1'-carbonyldiimidazole In tetrahydrofuran for 0.75h; Inert atmosphere;
Stage #3: 1-(4-carbamoylphenyl)-3-methyltriazene With sodium hydride; triethylamine In tetrahydrofuran; dichloromethane; mineral oil for 48h; Inert atmosphere;
56.2%
2-(bromomethyl)-4(3H)-quinazolinone
19062-51-2

2-(bromomethyl)-4(3H)-quinazolinone

sodium valproate
1069-66-5

sodium valproate

2-propylpentanoic acid 4-oxo-3,4-dihydroquinazolin-2-ylmethyl ester
1260163-35-6

2-propylpentanoic acid 4-oxo-3,4-dihydroquinazolin-2-ylmethyl ester

Conditions
ConditionsYield
In ethanol for 48h; Reflux;52%
1-(4-bromophenyl)-3-methyltriazene
40643-36-5

1-(4-bromophenyl)-3-methyltriazene

sodium valproate
1069-66-5

sodium valproate

1-(4-bromophenyl)-3-methyl-[2-(propyl)pentanoyl]triazene

1-(4-bromophenyl)-3-methyl-[2-(propyl)pentanoyl]triazene

Conditions
ConditionsYield
Stage #1: sodium valproate With benzotriazol-1-ol In tetrahydrofuran at 20℃; for 0.25h;
Stage #2: With 1,1'-carbonyldiimidazole In tetrahydrofuran for 0.75h; Inert atmosphere;
Stage #3: 1-(4-bromophenyl)-3-methyltriazene With sodium hydride; triethylamine In tetrahydrofuran; dichloromethane; mineral oil for 48h; Inert atmosphere;
46.1%

1069-66-5Relevant articles and documents

Synthesis, characterization and behavior in water/DMSO solution of Ru(II) arene complexes with bioactive carboxylates

Biancalana, Lorenzo,Pampaloni, Guido,Zacchini, Stefano,Marchetti, Fabio

, p. 201 - 211 (2018)

The reactions of [RuCl(μ-Cl)(η6-p-cymene)]2 with sodium carboxylates, in methanol or acetonitrile solution, afforded the complexes [RuCl(κ2O-RCO2)(η6-p-cymene)] (RCO2 = valproate, 1; aspirinate, 2; diclofenate, 3), in 79–96% yields. Analogously, [RuCl(κ2O-dfCO2)(η6-benzene)], 4, was obtained in admixture with minor by-products from [RuCl(μ-Cl)(η6-benzene)]2 and sodium/silver diclofenate. The sequential reaction of [RuCl(μ-Cl)(η6-p-cymene)]2 with sodium salicylate and PPh3 gave [Ru(κ2O,O′-salCO2)(PPh3)(η6-p-cymene)], 5, in 70% yield. The hydride complex [Ru2Cl2(μ-Cl)(μ-H)(η6-p-cymene)2], 6, was produced in 36% yield from [RuCl(μ-Cl)(η6-p-cymene)]2 and sodium formate. An optimization of the experimental work-up allowed to isolate [RuCl(μ-Cl)(η6-p-cymene)]2 with an improved yield respect to the literature (98% vs. 65%). The bidentate coordination mode of the carboxylato ligands in 1–5 was unambiguously ascertained by IR and NMR spectroscopy, moreover the solid state structure of 1 was elucidated by single crystal X-ray diffraction. Complexes 1–3 experience rapid and quantitative dissociation of the carboxylato anion in DMSO/water/NaCl mixtures, mainly converting into [RuCl2(DMSO)(η6-p-cymene)], 7.

Pharmaceutical composition with high safety, and preparation method thereof

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Paragraph 0029-0040, (2021/06/22)

The invention provides a pharmaceutical composition with high safety, which is characterized in that the pharmaceutical composition contains not less than 90% of sodium valproate and not more than 0.014% of 2-methylvaleric acid; and the content of the sodium valproate is preferably not less than 95% and more preferably not less than 99%. Meanwhile, the invention also provides a preparation method and application of the pharmaceutical composition. The sodium valproate pharmaceutical composition and the preparation thereof in the invention provide an effective solution for improving the safety and the stability of the medicine. Meanwhile, the preparation method of the sodium valproate pharmaceutical composition disclosed by the invention is simple in process, high in yield, high in purity and suitable for industrial mass production.

Vpa synthesis process (by machine translation)

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Paragraph 0010, (2017/03/17)

The invention discloses a process for synthesizing valproic acid sodium, comprises the following processes: malonic acid diethyl ester and 1- the bromine is positive propane mutual dissolution, the mixture is slowly added at certain temperature ethanol solution of sodium ethylate, heating reflux 2 hours, to recycle ethanol 110 °C, cooling to 80 °C the following, add quantitative a water-soluble sodium bromide, added after laminating a fresh keeping 15-30% aqueous sodium hydroxide solution, for 60-70 °C hydrolysis 3 hours, the gas temperature of the temperature recovery ethanol 99 °C, cooling to 80 °C the following, and in adding hydrochloric acid and dyeworks, adding crude valproic acid dissolving dipropyl malonic acid, mixed acid forming the, mixed acid for 110-160 °C decarboxylation slowly increase and produce crudely valproic acid. Valproic acid crude product after being refined after rectification, to neutralize the sodium hydroxide aqueous solution, adding toluene reflux with water, dewatering and crystallization of the valproic acid sodium, filtering, chlorofrom washing drying to obtain the finished product. The process safety and environmental protection, good quality, low cost, is suitable for industrial production. (by machine translation)

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