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Cas Database

33286-22-5

33286-22-5

Identification

  • Product Name:1,5-Benzothiazepin-4(5H)-one,3-(acetyloxy)-5-[2-(dimethylamino)ethyl]-2,3-dihydro-2-(4-methoxyphenyl)-,hydrochloride (1:1), (2S,3S)-

  • CAS Number: 33286-22-5

  • EINECS:251-443-3

  • Molecular Weight:450.986

  • Molecular Formula: C22H26N2O4S.HCl

  • HS Code:29349990

  • Mol File:33286-22-5.mol

Synonyms:1,5-Benzothiazepin-4(5H)-one,3-(acetyloxy)-5-[2-(dimethylamino)ethyl]-2,3-dihydro-2-(4-methoxyphenyl)-,monohydrochloride, (2S,3S)- (9CI);1,5-Benzothiazepin-4(5H)-one,3-(acetyloxy)-5-[2-(dimethylamino)ethyl]-2,3-dihydro-2-(4-methoxyphenyl)-,monohydrochloride, (2S-cis)-;(+)-Diltiazem hydrochloride;(2S,3S)-(+)-cis-Diltiazem hydrochloride;(S,S)-Diltiazem hydrochloride;Adizem;Altiazem;Anginyl;Blocalcin 60;Britiazim;CRD401;Calcicard;Cardizem SR;Dilacor XR;Diladel;Dilcardia;Dilgard;Dilzene;d-cis-3-Acetoxy-2,3-dihydro-5-[2-(dimethylamino)ethyl]-2-(p-methoxyphenyl)-1,5-benzothiazepin-4(5H)-onehydrochloride;d-cis-Diltiazem hydrochloride;

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Safety information and MSDS view more

  • Pictogram(s):HarmfulXn,IrritantXi

  • Hazard Codes:Xn,Xi,F

  • Signal Word:Warning

  • Hazard Statement:H302 Harmful if swallowed

  • First-aid measures: General adviceConsult a physician. Show this safety data sheet to the doctor in attendance.If inhaled If breathed in, move person into fresh air. If not breathing, give artificial respiration. Consult a physician. In case of skin contact Wash off with soap and plenty of water. Consult a physician. In case of eye contact Rinse thoroughly with plenty of water for at least 15 minutes and consult a physician. If swallowed Never give anything by mouth to an unconscious person. Rinse mouth with water. Consult a physician.

  • Fire-fighting measures: Suitable extinguishing media Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide. Wear self-contained breathing apparatus for firefighting if necessary.

  • Accidental release measures: Use personal protective equipment. Avoid dust formation. Avoid breathing vapours, mist or gas. Ensure adequate ventilation. Evacuate personnel to safe areas. Avoid breathing dust. For personal protection see section 8. Prevent further leakage or spillage if safe to do so. Do not let product enter drains. Discharge into the environment must be avoided. Pick up and arrange disposal. Sweep up and shovel. Keep in suitable, closed containers for disposal.

  • Handling and storage: Avoid contact with skin and eyes. Avoid formation of dust and aerosols. Avoid exposure - obtain special instructions before use.Provide appropriate exhaust ventilation at places where dust is formed. For precautions see section 2.2. Store in cool place. Keep container tightly closed in a dry and well-ventilated place.

  • Exposure controls/personal protection:Occupational Exposure limit valuesBiological limit values Handle in accordance with good industrial hygiene and safety practice. Wash hands before breaks and at the end of workday. Eye/face protection Safety glasses with side-shields conforming to EN166. Use equipment for eye protection tested and approved under appropriate government standards such as NIOSH (US) or EN 166(EU). Skin protection Wear impervious clothing. The type of protective equipment must be selected according to the concentration and amount of the dangerous substance at the specific workplace. Handle with gloves. Gloves must be inspected prior to use. Use proper glove removal technique(without touching glove's outer surface) to avoid skin contact with this product. Dispose of contaminated gloves after use in accordance with applicable laws and good laboratory practices. Wash and dry hands. The selected protective gloves have to satisfy the specifications of EU Directive 89/686/EEC and the standard EN 374 derived from it. Respiratory protection Wear dust mask when handling large quantities. Thermal hazards

Supplier and reference price

  • Manufacture/Brand
  • Product Description
  • Packaging
  • Price
  • Delivery
  • Purchase
  • Manufacture/Brand:TRC
  • Product Description:Diltiazem, Hydrochloride
  • Packaging:10g
  • Price:$ 220
  • Delivery:In stock
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  • Manufacture/Brand:Tocris
  • Product Description:Diltiazem, Hydrochloride ≥99%(HPLC)
  • Packaging:1G
  • Price:$ 107
  • Delivery:In stock
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  • Manufacture/Brand:TCI Chemical
  • Product Description:(+)-cis-Diltiazem Hydrochloride >98.0%(HPLC)(T)
  • Packaging:25g
  • Price:$ 259
  • Delivery:In stock
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  • Manufacture/Brand:TCI Chemical
  • Product Description:(+)-cis-Diltiazem Hydrochloride >98.0%(HPLC)(T)
  • Packaging:5g
  • Price:$ 74
  • Delivery:In stock
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  • Manufacture/Brand:Sigma-Aldrich
  • Product Description:Diltiazem hydrochloride solution 1.0 mg/mL in acetonitrile (as free base), ampule of 1 mL, certified reference material
  • Packaging:035-1ml
  • Price:$ 27.9
  • Delivery:In stock
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  • Manufacture/Brand:Sigma-Aldrich
  • Product Description:Diltiazem hydrochloride solution 1.0?mg/mL in acetonitrile (as free base), ampule of 1?mL, certified reference material, Cerilliant?
  • Packaging:1 mL
  • Price:$ 28.8
  • Delivery:In stock
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  • Manufacture/Brand:Sigma-Aldrich
  • Product Description:(+)-cis-Diltiazem hydrochloride ≥99% (HPLC)
  • Packaging:1g
  • Price:$ 92.6
  • Delivery:In stock
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  • Manufacture/Brand:Sigma-Aldrich
  • Product Description:Diltiazem, Hydrochloride Synthetic benzothiazepine that acts as an L-type Ca
  • Packaging:100mg
  • Price:$ 74.92
  • Delivery:In stock
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  • Manufacture/Brand:Sigma-Aldrich
  • Product Description:Diltiazem hydrochloride European Pharmacopoeia (EP) Reference Standard
  • Packaging:
  • Price:$ 190
  • Delivery:In stock
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  • Manufacture/Brand:Sigma-Aldrich
  • Product Description:Diltiazem for system suitability European Pharmacopoeia (EP) Reference Standard
  • Packaging:y0001141
  • Price:$ 190
  • Delivery:In stock
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Relevant articles and documentsAll total 11 Articles be found

Process for preparing diltiazem using a heterogeneous trifunctional catalyst

-

Page 4, (2008/06/13)

The present invention comprises a simplified synthesis of (+)-diltiazem through IE-PdOsW wherein IE is ion-exchanger, catalyzed three-component coupling reaction and Fe3+-exchanged clay catalyzed ring opening of sulfite with 2-aminothiophenol followed by cyclization as key steps.

PROCESS FOR PREPARING DILTIAZEM USING A HETEROGENEOUS TRIFUNCTIONAL CATALYST

-

Page 7-8, (2008/06/13)

The present invention comprises a simplified synthesis of (+)-diltiazem through IE-PdOsW wherein IE is ion-exchanger, catalyzed three-component coupling reaction and Fe3+-exchanged clay catalyzed ring opening of sulfite with 2-aminothiophenol followed by cyclization as key steps.

Improved procedure for Julia-Colonna asymmetric epoxidation of α,β-unsaturated ketones: Total synthesis of diltiazem and Taxol side-chain

Adger, Brian M.,Barkley, James V.,Bergeron, Sophie,Cappi, Michael W.,Flowerdew, Benjamin E.,Jackson, Mark P.,McCague, Ray,Nugent, Thomas C.,Roberts, Stanley M.

, p. 3501 - 3507 (2007/10/03)

Poly-L-leucine catalyses the asymmetric epoxidation of enones 1-6 efficiently in a non-aqueous medium to provide the epoxy ketones 7-12 (70-91% yield; 80 to ≥95% ee). The strategy was used to make diltiazem 16 and the Taxol side chain 23 in single enantiomer form.

Process for the preparation of diltiazem

-

, (2008/06/13)

(+)-Cis-3-(acetoxy)-5-[2-(dimethylamino)-ethyl]-2,3-dihydro-2-(4-methoxyphenyl)-1,5-benzothiazepin-4(5H)-one hydrochloride is prepared by N-alkylation of (+)-cis-3-hydroxy-2,3-dihydro-2-(4-methoxyphenyl)-1,5-benzothiazepin-4(5H)-one with dimethylaminoethyl chloride and K2 CO3 in toluene/water, addition of a solubilizing agent and in the presence of a phase-transfer catalyst, the toluene phase being directly subjected to the final O-- acetylation.

Process for the preparation of benzothiazepin-one derivatives

-

, (2008/06/13)

The object of the invention is a process for the preparation of the trans(-) (2R,3S) diastereoisomer of the glycidic esters of general formula: STR1 wherein a chlorohydrin of general formula: STR2 is reacted with a strong organic base in a suitable solvent and at a temperature between -10° C. and room temperature. Another object of the invention is intermediate compounds cis(+) (2S,3S) 1,5-benzothiazepin-4-one.

Process route upstream and downstream products

Process route

diltiazem
42399-41-7

diltiazem

diltiazem hydrochloride
33286-22-5

diltiazem hydrochloride

Conditions
Conditions Yield
O-desacetyldiltiazem
42399-40-6

O-desacetyldiltiazem

acetic anhydride
108-24-7

acetic anhydride

diltiazem hydrochloride
33286-22-5

diltiazem hydrochloride

Conditions
Conditions Yield
O-desacetyldiltiazem; acetic anhydride; With dmap; triethylamine; In dichloromethane; for 3h; Heating / reflux;
With hydrogenchloride; In methanol; pH=2;
92%
With hydrogenchloride; In ethanol; butanone; at 90 ℃; for 1h;
80%
With dmap; In dichloromethane; for 3h; Yield given; Heating;
(2S,3S)-5-(2-dimethylaminoethyl)-3-hydroxy-2-(4-methoxyphenyl)-2,3-dihydro-1,5-benzothiazepin-4(5H)-one hydrochloride
75472-91-2

(2S,3S)-5-(2-dimethylaminoethyl)-3-hydroxy-2-(4-methoxyphenyl)-2,3-dihydro-1,5-benzothiazepin-4(5H)-one hydrochloride

acetic anhydride
108-24-7

acetic anhydride

diltiazem hydrochloride
33286-22-5

diltiazem hydrochloride

Conditions
Conditions Yield
(2S,3S)-5-(2-dimethylaminoethyl)-3-hydroxy-2-(4-methoxyphenyl)-2,3-dihydro-1,5-benzothiazepin-4(5H)-one hydrochloride; acetic anhydride; With dmap; triethylamine; In dichloromethane;
With hydrogenchloride; In methanol; pH=2;
92%
With pyridine; dmap;
Isopropenyl acetate
108-22-5

Isopropenyl acetate

(2S,3S)-5-(2-dimethylaminoethyl)-3-hydroxy-2-(4-methoxyphenyl)-2,3-dihydro-1,5-benzothiazepin-4(5H)-one hydrochloride
75472-91-2

(2S,3S)-5-(2-dimethylaminoethyl)-3-hydroxy-2-(4-methoxyphenyl)-2,3-dihydro-1,5-benzothiazepin-4(5H)-one hydrochloride

diltiazem hydrochloride
33286-22-5

diltiazem hydrochloride

Conditions
Conditions Yield
With methanesulfonic acid; In chloroform; for 0.75h; Heating;
88.8%
(2S,3S)-3-hydroxy-2-(4-methoxyphenyl)-2,3-dihydro-1,5-benzothiazepin-4(5H)-one
42399-49-5

(2S,3S)-3-hydroxy-2-(4-methoxyphenyl)-2,3-dihydro-1,5-benzothiazepin-4(5H)-one

diltiazem hydrochloride
33286-22-5

diltiazem hydrochloride

Conditions
Conditions Yield
Multi-step reaction with 2 steps
1: K2CO3 / ethyl acetate
2: pyridine, DMAP
With pyridine; dmap; potassium carbonate; In ethyl acetate;
Multi-step reaction with 2 steps
1: 67 percent / NaH / dimethylformamide; paraffin; diethyl ether / 3 h / 70 °C
2: 80 percent / 2.) HCl / butan-2-one; ethanol / 1 h / 90 °C
With hydrogenchloride; sodium hydride; In diethyl ether; ethanol; N,N-dimethyl-formamide; butanone; paraffin;
Multi-step reaction with 2 steps
1: 88.2 percent / K2CO3 / H2O; ethyl acetate / 5 h / Heating
2: DMAP / CH2Cl2 / 3 h / Heating
With dmap; potassium carbonate; In dichloromethane; water; ethyl acetate;
(αS,βS,1R,2S)-β-<(2-aminophenyl)thio>-α-hydroxy-β-(4-methoxyphenyl)propanoic acid 2-phenylcyclohexyl ester hydrochloride
138382-02-2

(αS,βS,1R,2S)-β-<(2-aminophenyl)thio>-α-hydroxy-β-(4-methoxyphenyl)propanoic acid 2-phenylcyclohexyl ester hydrochloride

diltiazem hydrochloride
33286-22-5

diltiazem hydrochloride

Conditions
Conditions Yield
Multi-step reaction with 4 steps
1: 81 percent / 2 N NaOH / ethanol; H2O / 2 h / Heating
2: 88 percent / PTSA / xylene / 16 h / Heating
3: 88.2 percent / K2CO3 / H2O; ethyl acetate / 5 h / Heating
4: DMAP / CH2Cl2 / 3 h / Heating
With dmap; sodium hydroxide; potassium carbonate; toluene-4-sulfonic acid; In ethanol; dichloromethane; water; ethyl acetate; xylene;
Multi-step reaction with 3 steps
1: 73.2 percent / PTSA / xylene / 16 h / Heating
2: 88.2 percent / K2CO3 / H2O; ethyl acetate / 5 h / Heating
3: DMAP / CH2Cl2 / 3 h / Heating
With dmap; potassium carbonate; toluene-4-sulfonic acid; In dichloromethane; water; ethyl acetate; xylene;
(2S,3S)-threo-2-hydroxy-3-(2-aminophenylthio)-3-(4-methoxyphenyl)-propionic acid
42399-48-4

(2S,3S)-threo-2-hydroxy-3-(2-aminophenylthio)-3-(4-methoxyphenyl)-propionic acid

diltiazem hydrochloride
33286-22-5

diltiazem hydrochloride

Conditions
Conditions Yield
Multi-step reaction with 3 steps
1: 88 percent / PTSA / xylene / 16 h / Heating
2: 88.2 percent / K2CO3 / H2O; ethyl acetate / 5 h / Heating
3: DMAP / CH2Cl2 / 3 h / Heating
With dmap; potassium carbonate; toluene-4-sulfonic acid; In dichloromethane; water; ethyl acetate; xylene;
(E)-1-(4-methoxyphenyl)-4,4-dimethylpent-1-en-3-one
2419-67-2,24470-83-5,41564-61-8

(E)-1-(4-methoxyphenyl)-4,4-dimethylpent-1-en-3-one

diltiazem hydrochloride
33286-22-5

diltiazem hydrochloride

Conditions
Conditions Yield
Multi-step reaction with 6 steps
1: 70 percent / urea hydrogen peroxide, DBU, immobilised poly-L-leucine / tetrahydrofuran / 28 h
2: 84 percent / MCPBA, KF / CH2Cl2 / 24 h
3: 90 percent / toluene / 17 h / Heating
4: 94 percent / xylene / 216 h / Heating
5: K2CO3 / ethyl acetate
6: pyridine, DMAP
With pyridine; dmap; potassium fluoride; immobilised poly-L-leucine; urea hydrogen peroxide; potassium carbonate; 1,8-diazabicyclo[5.4.0]undec-7-ene; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; dichloromethane; ethyl acetate; toluene; xylene;
4-methoxy-benzaldehyde
123-11-5

4-methoxy-benzaldehyde

diltiazem hydrochloride
33286-22-5

diltiazem hydrochloride

Conditions
Conditions Yield
Multi-step reaction with 7 steps
1: 87 percent / NaOMe / methanol / 40 h / Heating
2: 70 percent / urea hydrogen peroxide, DBU, immobilised poly-L-leucine / tetrahydrofuran / 28 h
3: 84 percent / MCPBA, KF / CH2Cl2 / 24 h
4: 90 percent / toluene / 17 h / Heating
5: 94 percent / xylene / 216 h / Heating
6: K2CO3 / ethyl acetate
7: pyridine, DMAP
With pyridine; dmap; potassium fluoride; immobilised poly-L-leucine; urea hydrogen peroxide; sodium methylate; potassium carbonate; 1,8-diazabicyclo[5.4.0]undec-7-ene; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; methanol; dichloromethane; ethyl acetate; toluene; xylene;
tert-butyl (2R,3S)-3-(4-methoxyphenyl)glycidate
201804-22-0

tert-butyl (2R,3S)-3-(4-methoxyphenyl)glycidate

diltiazem hydrochloride
33286-22-5

diltiazem hydrochloride

Conditions
Conditions Yield
Multi-step reaction with 4 steps
1: 90 percent / toluene / 17 h / Heating
2: 94 percent / xylene / 216 h / Heating
3: K2CO3 / ethyl acetate
4: pyridine, DMAP
With pyridine; dmap; potassium carbonate; In ethyl acetate; toluene; xylene;

Global suppliers and manufacturers

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  • Hangzhou Dingyan Chem Co., Ltd
  • Business Type:Trading Company
  • Contact Tel:86-571-86465881,86-571-87157530,86-571-88025800
  • Emails:sales@dingyanchem.com
  • Main Products:95
  • Country:China (Mainland)
  • Chemwill Asia Co., Ltd.
  • Business Type:Manufacturers
  • Contact Tel:021-51086038
  • Emails:sales@chemwill.com
  • Main Products:30
  • Country:China (Mainland)
  • Amadis Chemical Co., Ltd.
  • Business Type:Lab/Research institutions
  • Contact Tel:86-571-89925085
  • Emails:sales@amadischem.com
  • Main Products:29
  • Country:China (Mainland)
  • Shaanxi BLOOM TECH Co.,Ltd
  • Business Type:Lab/Research institutions
  • Contact Tel:+86-29-86470566
  • Emails:sales@bloomtechz.com
  • Main Products:80
  • Country:China (Mainland)
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