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33016-47-6 Usage

Uses

1-Tritylimidazole-4-carboxaldehyde is used in the synthesis of histamine and girolline

Check Digit Verification of cas no

The CAS Registry Mumber 33016-47-6 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 3,3,0,1 and 6 respectively; the second part has 2 digits, 4 and 7 respectively.
Calculate Digit Verification of CAS Registry Number 33016-47:
(7*3)+(6*3)+(5*0)+(4*1)+(3*6)+(2*4)+(1*7)=76
76 % 10 = 6
So 33016-47-6 is a valid CAS Registry Number.
InChI:InChI=1/C23H18N2O/c26-17-22-16-25(18-24-22)23(19-10-4-1-5-11-19,20-12-6-2-7-13-20)21-14-8-3-9-15-21/h1-18H

33016-47-6 Well-known Company Product Price

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  • Alfa Aesar

  • (B25272)  1-Tritylimidazole-4-carboxaldehyde, 98%   

  • 33016-47-6

  • 1g

  • 384.0CNY

  • Detail
  • Alfa Aesar

  • (B25272)  1-Tritylimidazole-4-carboxaldehyde, 98%   

  • 33016-47-6

  • 5g

  • 1416.0CNY

  • Detail
  • Alfa Aesar

  • (B25272)  1-Tritylimidazole-4-carboxaldehyde, 98%   

  • 33016-47-6

  • 25g

  • 5584.0CNY

  • Detail

33016-47-6SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 11, 2017

Revision Date: Aug 11, 2017

1.Identification

1.1 GHS Product identifier

Product name 1-tritylimidazole-4-carbaldehyde

1.2 Other means of identification

Product number -
Other names 1-triphenylmethyl-4-imidazolyl carboxaldehyde

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:33016-47-6 SDS

33016-47-6Synthetic route

trityl chloride
76-83-5

trityl chloride

4(5)formylimidazole
3034-50-2

4(5)formylimidazole

(1-tritylimidazol-4-yl)carboxaldehyde
33016-47-6

(1-tritylimidazol-4-yl)carboxaldehyde

Conditions
ConditionsYield
With triethylamine In dichloromethane at 20℃;100%
With triethylamine In N,N-dimethyl-formamide at 0 - 20℃;100%
With triethylamine In N,N-dimethyl-formamide at 20℃;99%
5-imidazolecarboxaldehyde
3034-50-2

5-imidazolecarboxaldehyde

trityl chloride
76-83-5

trityl chloride

(1-tritylimidazol-4-yl)carboxaldehyde
33016-47-6

(1-tritylimidazol-4-yl)carboxaldehyde

Conditions
ConditionsYield
In dichloromethane at 0 - 20℃;98%
With triethylamine In acetonitrile at 20℃;94%
With triethylamine In acetonitrile at 20℃; for 20.3333h;94%
4-(hydroxymethyl)-1-(triphenylmethyl)imidazole
33769-07-2

4-(hydroxymethyl)-1-(triphenylmethyl)imidazole

(1-tritylimidazol-4-yl)carboxaldehyde
33016-47-6

(1-tritylimidazol-4-yl)carboxaldehyde

Conditions
ConditionsYield
With manganese(IV) oxide In 1,4-dioxane for 5h; Heating;95%
With oxalyl dichloride; dimethyl sulfoxide In dichloromethane at -70℃; for 0.333333h;82%
With Mn2O In 1,4-dioxane at 85℃; for 6h;80%
N-trityl-4(5)-iodoimidazole
96797-15-8

N-trityl-4(5)-iodoimidazole

N,N-dimethyl-formamide
68-12-2, 33513-42-7

N,N-dimethyl-formamide

A

1-tritylimidazole-2,4-dicarboxaldehyde
96797-16-9

1-tritylimidazole-2,4-dicarboxaldehyde

B

1-(triphenylmethyl)-1H-imidazole-2-carboxaldehyde
67478-50-6

1-(triphenylmethyl)-1H-imidazole-2-carboxaldehyde

C

(1-tritylimidazol-4-yl)carboxaldehyde
33016-47-6

(1-tritylimidazol-4-yl)carboxaldehyde

Conditions
ConditionsYield
With n-butyllithium In tetrahydrofuran; hexane Product distribution; cooling in a dry ice acetone bath, excess n-BuLi;A 8 mg
B 11%
C 83%
With n-butyllithium 1.) THF, hexane, 5 s, cooling in a dry ice acetone bath; Yield given. Multistep reaction. Yields of byproduct given;
N-trityl-4(5)-iodoimidazole
96797-15-8

N-trityl-4(5)-iodoimidazole

N,N-dimethyl-formamide
68-12-2, 33513-42-7

N,N-dimethyl-formamide

(1-tritylimidazol-4-yl)carboxaldehyde
33016-47-6

(1-tritylimidazol-4-yl)carboxaldehyde

Conditions
ConditionsYield
Stage #1: N-trityl-4(5)-iodoimidazole With ethylmagnesium bromide In diethyl ether; dichloromethane at 20℃; for 0.5h;
Stage #2: N,N-dimethyl-formamide In diethyl ether; dichloromethane at 20℃; for 0.5h;
82%
Stage #1: N-trityl-4(5)-iodoimidazole With ethylmagnesium bromide In dichloromethane
Stage #2: N,N-dimethyl-formamide In dichloromethane at 20℃;
82%
Stage #1: N-trityl-4(5)-iodoimidazole With isopropylmagnesium chloride In dichloromethane at 10 - 20℃;
Stage #2: N,N-dimethyl-formamide In dichloromethane at -5 - 20℃; for 10.5h;
Stage #3: With water; ammonium chloride In dichloromethane at 20℃;
73.2%
N-trityl-4(5)-iodoimidazole
96797-15-8

N-trityl-4(5)-iodoimidazole

N,N-dimethyl-formamide
68-12-2, 33513-42-7

N,N-dimethyl-formamide

A

N-tritylimidazole
15469-97-3

N-tritylimidazole

B

4-iodo-2-formyl-1-tritylimidazole

4-iodo-2-formyl-1-tritylimidazole

C

1-(triphenylmethyl)-1H-imidazole-2-carboxaldehyde
67478-50-6

1-(triphenylmethyl)-1H-imidazole-2-carboxaldehyde

D

(1-tritylimidazol-4-yl)carboxaldehyde
33016-47-6

(1-tritylimidazol-4-yl)carboxaldehyde

Conditions
ConditionsYield
With n-butyllithium In tetrahydrofuran; hexane Product distribution; cooling in a dry ice acetone bath, stoichiometric n-BuLi;A 19%
B 16%
C 7%
D 51%
With n-butyllithium 1.) THF, hexane, 5 s, cooling in a dry ice acetone bath; Yield given. Multistep reaction. Yields of byproduct given;
N-Formylpiperidine
2591-86-8

N-Formylpiperidine

N-trityl-4(5)-iodoimidazole
96797-15-8

N-trityl-4(5)-iodoimidazole

(1-tritylimidazol-4-yl)carboxaldehyde
33016-47-6

(1-tritylimidazol-4-yl)carboxaldehyde

Conditions
ConditionsYield
With ethylmagnesium bromide 1.) THF, Et2O, room temp., 30 min., 2.) 1 h; Yield given. Multistep reaction;
trityl chloride
76-83-5

trityl chloride

amalgamated silver

amalgamated silver

(1-tritylimidazol-4-yl)carboxaldehyde
33016-47-6

(1-tritylimidazol-4-yl)carboxaldehyde

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 94 percent / TEA / dimethylformamide
View Scheme
trityl chloride
76-83-5

trityl chloride

Me-X

Me-X

(1-tritylimidazol-4-yl)carboxaldehyde
33016-47-6

(1-tritylimidazol-4-yl)carboxaldehyde

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: imidazole / dimethylformamide
2: MnO2 / dioxane
View Scheme
trityl chloride
76-83-5

trityl chloride

DL-lysine methyl ester dihydrochloride

DL-lysine methyl ester dihydrochloride

(1-tritylimidazol-4-yl)carboxaldehyde
33016-47-6

(1-tritylimidazol-4-yl)carboxaldehyde

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 93 percent / Et3N / dimethylformamide / 18 h
2: 80 percent / Mn2O / dioxane / 6 h / 85 °C
View Scheme
trityl chloride
76-83-5

trityl chloride

(1-tritylimidazol-4-yl)carboxaldehyde
33016-47-6

(1-tritylimidazol-4-yl)carboxaldehyde

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: Et3N / dimethylformamide
2: MnO2 / dioxane
View Scheme
With triethylamine In dichloromethane; water
With triethylamine In N,N-dimethyl-formamide; benzene
1-trityl-1H-imidazole-4-carboxaldehyde resin

1-trityl-1H-imidazole-4-carboxaldehyde resin

(1-tritylimidazol-4-yl)carboxaldehyde
33016-47-6

(1-tritylimidazol-4-yl)carboxaldehyde

Conditions
ConditionsYield
With trifluoroacetic acid In dichloromethane trityl chloride resin;
(1-tritylimidazol-4-yl)carboxaldehyde
33016-47-6

(1-tritylimidazol-4-yl)carboxaldehyde

1-(5-fluoro-3-methylbenzo[b]thiophen-2-yl)ethanone
51828-34-3

1-(5-fluoro-3-methylbenzo[b]thiophen-2-yl)ethanone

(E)-1-(5-fluoro-3-methylbenzo[b]thiophen-2-yl)-3-(1-triphenylmethyl-1H-imidazol-4-yl)-2-propen-1-one
212078-55-2

(E)-1-(5-fluoro-3-methylbenzo[b]thiophen-2-yl)-3-(1-triphenylmethyl-1H-imidazol-4-yl)-2-propen-1-one

Conditions
ConditionsYield
With sodium hydroxide In tetrahydrofuran; methanol at 20℃; for 4h; Claisen-Schmidt reaction;100%
Nitroethane
79-24-3

Nitroethane

(1-tritylimidazol-4-yl)carboxaldehyde
33016-47-6

(1-tritylimidazol-4-yl)carboxaldehyde

4-(2-nitro-propenyl)-1-trityl-1H-imidazole

4-(2-nitro-propenyl)-1-trityl-1H-imidazole

Conditions
ConditionsYield
With ammonium acetate for 6h; Henry reaction; Reflux;100%
ammonium chloride

ammonium chloride

2-oxopiperidine-1-carboxylic acid tert-butyl ester
85908-96-9

2-oxopiperidine-1-carboxylic acid tert-butyl ester

(1-tritylimidazol-4-yl)carboxaldehyde
33016-47-6

(1-tritylimidazol-4-yl)carboxaldehyde

tert-Butyl 3-[hydroxy(1-trityl-1H-imidazol-4-yl)methyl]-2-oxo-1-piperidinecarboxylate

tert-Butyl 3-[hydroxy(1-trityl-1H-imidazol-4-yl)methyl]-2-oxo-1-piperidinecarboxylate

Conditions
ConditionsYield
With lithium diisopropyl amide In tetrahydrofuran; cyclohexane99%
2-aminoethylpyridine
42088-91-5

2-aminoethylpyridine

(1-tritylimidazol-4-yl)carboxaldehyde
33016-47-6

(1-tritylimidazol-4-yl)carboxaldehyde

1-(pyridin-2-yl)-N-((1-trityl-1H-imidazol-4-yl)methylene)ethanamine

1-(pyridin-2-yl)-N-((1-trityl-1H-imidazol-4-yl)methylene)ethanamine

Conditions
ConditionsYield
In ethanol at 0 - 20℃;99%
(1-tritylimidazol-4-yl)carboxaldehyde
33016-47-6

(1-tritylimidazol-4-yl)carboxaldehyde

4(5)formylimidazole
3034-50-2

4(5)formylimidazole

Conditions
ConditionsYield
With acetic acid In methanol for 7h; Heating;98%
With acetic acid In methanol for 13h; Heating;82%
methylmagnesium bromide
75-16-1

methylmagnesium bromide

(1-tritylimidazol-4-yl)carboxaldehyde
33016-47-6

(1-tritylimidazol-4-yl)carboxaldehyde

alpha-methyl-1-triphenylmethyl-1H-imidazole-4-methanol
62256-50-2

alpha-methyl-1-triphenylmethyl-1H-imidazole-4-methanol

Conditions
ConditionsYield
In tetrahydrofuran; diethyl ether for 1h; Grignard reaction;98%
Stage #1: methylmagnesium bromide; (1-tritylimidazol-4-yl)carboxaldehyde In tetrahydrofuran; hexane at 0 - 20℃;
Stage #2: With water; ammonium chloride In tetrahydrofuran; hexane
75%
In tetrahydrofuran; diethyl ether at 20℃; for 1.5h;
Stage #1: methylmagnesium bromide; (1-tritylimidazol-4-yl)carboxaldehyde In tetrahydrofuran; diethyl ether at 15℃; for 4h;
Stage #2: With water; ammonium chloride In tetrahydrofuran; diethyl ether
benzylamine
100-46-9

benzylamine

(1-tritylimidazol-4-yl)carboxaldehyde
33016-47-6

(1-tritylimidazol-4-yl)carboxaldehyde

C30H27N3
186422-32-2

C30H27N3

Conditions
ConditionsYield
Stage #1: benzylamine; (1-tritylimidazol-4-yl)carboxaldehyde With sodium acetate In methanol at 20℃;
Stage #2: With sodium tetrahydroborate for 4h;
98%
With sodium tetrahydroborate; sodium acetate In methanol at 20℃; 3°A molecular sieves;98%
With sodium tris(acetoxy)borohydride In dichloromethane at 20℃;
3-[2-(aminomethyl)-5-chlorophenyl]propanoic acid hydrochloride
1076192-18-1

3-[2-(aminomethyl)-5-chlorophenyl]propanoic acid hydrochloride

(1-tritylimidazol-4-yl)carboxaldehyde
33016-47-6

(1-tritylimidazol-4-yl)carboxaldehyde

3-[5-chloro-2-({[(1-trityl-1H-imidazol-4-yl)methyl]amino}methyl)phenyl]propanoic acid
1076192-20-5

3-[5-chloro-2-({[(1-trityl-1H-imidazol-4-yl)methyl]amino}methyl)phenyl]propanoic acid

Conditions
ConditionsYield
Stage #1: 3-[2-(aminomethyl)-5-chlorophenyl]propanoic acid hydrochloride; (1-tritylimidazol-4-yl)carboxaldehyde With triethylamine; trimethyl orthoformate In methanol at 20℃; for 16h;
Stage #2: With sodium tetrahydroborate In methanol for 1h;
Stage #3: With sodium hydrogencarbonate In methanol; water pH=5 - 6;
96%
diethoxyphosphoryl-acetic acid ethyl ester
867-13-0

diethoxyphosphoryl-acetic acid ethyl ester

(1-tritylimidazol-4-yl)carboxaldehyde
33016-47-6

(1-tritylimidazol-4-yl)carboxaldehyde

(E)-3-(1-triphenylmethyl-1H-imidazol-4-yl)-2-propenoic acid ethyl ester
111157-50-7

(E)-3-(1-triphenylmethyl-1H-imidazol-4-yl)-2-propenoic acid ethyl ester

Conditions
ConditionsYield
With potassium hydroxide In tetrahydrofuran Ambient temperature;95%
vinyl magnesium bromide
1826-67-1

vinyl magnesium bromide

(1-tritylimidazol-4-yl)carboxaldehyde
33016-47-6

(1-tritylimidazol-4-yl)carboxaldehyde

1-(1-trityl-1H-imidazol-4-yl)-prop-2-en-1-ol
127798-61-2

1-(1-trityl-1H-imidazol-4-yl)-prop-2-en-1-ol

Conditions
ConditionsYield
In tetrahydrofuran for 12h; Ambient temperature;94%
In tetrahydrofuran at -10℃;87%
In tetrahydrofuran Grignard reaction;41%
phenylmagnesium bromide
100-58-3

phenylmagnesium bromide

(1-tritylimidazol-4-yl)carboxaldehyde
33016-47-6

(1-tritylimidazol-4-yl)carboxaldehyde

1-triphenylmethyl-4-[(1-hydroxy-1-phenyl)methyl]-1H-imidazole
135773-27-2

1-triphenylmethyl-4-[(1-hydroxy-1-phenyl)methyl]-1H-imidazole

Conditions
ConditionsYield
With manganese dioxide In tetrahydrofuran; 1,4-dioxane94%
(1-tritylimidazol-4-yl)carboxaldehyde
33016-47-6

(1-tritylimidazol-4-yl)carboxaldehyde

methyl trifluoromethanesulfonate
333-27-7

methyl trifluoromethanesulfonate

3-methyl-3H-imidazole-4-carboxaldehyde trifluoromethanesulfonate

3-methyl-3H-imidazole-4-carboxaldehyde trifluoromethanesulfonate

Conditions
ConditionsYield
In dichloromethane at 20℃;93%
diethyl (cyanomethyl)phosphonate

diethyl (cyanomethyl)phosphonate

(1-tritylimidazol-4-yl)carboxaldehyde
33016-47-6

(1-tritylimidazol-4-yl)carboxaldehyde

1-trityl-4-(2-cyanoethyl)imidazole
154312-79-5

1-trityl-4-(2-cyanoethyl)imidazole

Conditions
ConditionsYield
With sodium amide In tetrahydrofuran 1.) room temperature, 1 h, 2.) reflux, 20 h;92%
2-(1,3-dioxoisoindolin-2-yl)ethyltriphenylphosphonium bromide
65273-64-5

2-(1,3-dioxoisoindolin-2-yl)ethyltriphenylphosphonium bromide

(1-tritylimidazol-4-yl)carboxaldehyde
33016-47-6

(1-tritylimidazol-4-yl)carboxaldehyde

(E)-N-[3-(1-Triphenylmethyl-1H-imidazol-4-yl)allyl]phthalimid
112547-04-3

(E)-N-[3-(1-Triphenylmethyl-1H-imidazol-4-yl)allyl]phthalimid

Conditions
ConditionsYield
With potassium tert-butylate In tetrahydrofuran at 0 - 60℃; for 3h;92%
[3-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-propyl]-triphenyl-phosphonium bromide
7743-29-5

[3-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-propyl]-triphenyl-phosphonium bromide

(1-tritylimidazol-4-yl)carboxaldehyde
33016-47-6

(1-tritylimidazol-4-yl)carboxaldehyde

2-[(E)-4-(1-Trityl-1H-imidazol-4-yl)-but-3-enyl]-isoindole-1,3-dione

2-[(E)-4-(1-Trityl-1H-imidazol-4-yl)-but-3-enyl]-isoindole-1,3-dione

Conditions
ConditionsYield
With potassium tert-butylate In tetrahydrofuran at 0 - 60℃; for 3h;92%
(4-phthalimidobutyl)triphenylphosphonium bromide
65273-47-4

(4-phthalimidobutyl)triphenylphosphonium bromide

(1-tritylimidazol-4-yl)carboxaldehyde
33016-47-6

(1-tritylimidazol-4-yl)carboxaldehyde

2-[(E)-5-(1-Trityl-1H-imidazol-4-yl)-pent-4-enyl]-isoindole-1,3-dione

2-[(E)-5-(1-Trityl-1H-imidazol-4-yl)-pent-4-enyl]-isoindole-1,3-dione

Conditions
ConditionsYield
With potassium tert-butylate In tetrahydrofuran at 0 - 60℃; for 3h;92%
diethyl 1-cyanomethylphosphonate
2537-48-6

diethyl 1-cyanomethylphosphonate

(1-tritylimidazol-4-yl)carboxaldehyde
33016-47-6

(1-tritylimidazol-4-yl)carboxaldehyde

1-trityl-4-(2-cyanoethyl)imidazole
154312-79-5

1-trityl-4-(2-cyanoethyl)imidazole

Conditions
ConditionsYield
Stage #1: (1-tritylimidazol-4-yl)carboxaldehyde With sodium amide In tetrahydrofuran
Stage #2: diethyl 1-cyanomethylphosphonate In tetrahydrofuran at 20℃;
92%
With sodium amide In tetrahydrofuran Heating;
ethyl bromozincacetate;THF

ethyl bromozincacetate;THF

(1-tritylimidazol-4-yl)carboxaldehyde
33016-47-6

(1-tritylimidazol-4-yl)carboxaldehyde

ethyl 3-hydroxy-3-(1-trityl-1H-imidazol-4-yl)propanoate
426219-40-1

ethyl 3-hydroxy-3-(1-trityl-1H-imidazol-4-yl)propanoate

Conditions
ConditionsYield
Stage #1: 1-triphenylmethyl-5-imidazolecarboxaldehyde; ethyl bromozincacetate;THF In tetrahydrofuran at 0 - 6℃; for 1.41667h;
Stage #2: ethyl bromozincacetate;THF In tetrahydrofuran at 0 - 3℃; for 5.5h;
Stage #3: With hydrogenchloride In tetrahydrofuran; water at 20℃;
92%
2,3-dimethylbromobenzene
576-23-8

2,3-dimethylbromobenzene

(1-tritylimidazol-4-yl)carboxaldehyde
33016-47-6

(1-tritylimidazol-4-yl)carboxaldehyde

4-<(2,3-dimethylphenyl)hydroxymethyl>-1-(triphenylmethyl)imidazole
176721-01-0

4-<(2,3-dimethylphenyl)hydroxymethyl>-1-(triphenylmethyl)imidazole

Conditions
ConditionsYield
Stage #1: 2,3-dimethylbromobenzene With iodine; magnesium In tetrahydrofuran at 70℃; for 1.5h; Inert atmosphere;
Stage #2: (1-tritylimidazol-4-yl)carboxaldehyde In tetrahydrofuran at -5 - 20℃; Inert atmosphere;
91.1%
Stage #1: 2,3-dimethylbromobenzene With iodine; magnesium In tetrahydrofuran for 1h; Reflux;
Stage #2: (1-tritylimidazol-4-yl)carboxaldehyde In tetrahydrofuran at 0 - 20℃; for 1.5h;
53.9%
With iodine; magnesium 1.) THF, reflux, 1 h, 2.) r.t., THF, 1.5 h; Yield given. Multistep reaction;
Stage #1: 2,3-dimethylbromobenzene With magnesium In tetrahydrofuran
Stage #2: (1-tritylimidazol-4-yl)carboxaldehyde In tetrahydrofuran at 0℃;
nitromethane
75-52-5

nitromethane

(1-tritylimidazol-4-yl)carboxaldehyde
33016-47-6

(1-tritylimidazol-4-yl)carboxaldehyde

4-(E)-(2-nitroethenyl)-1-(triphenylmethyl)-1H-imidazole
139285-03-3

4-(E)-(2-nitroethenyl)-1-(triphenylmethyl)-1H-imidazole

Conditions
ConditionsYield
With piperidine; acetic acid Ambient temperature;91%
With piperidine; acetic acid at 20℃; for 10h;82%
With piperidine; acetic acid at 20℃; for 8h;79%
With ammonium acetate In acetic acid at 22℃; for 6h; Knovenagel condensation; sonication;52%
With piperidine; acetic acid at 20℃; for 18h;
sodium chlorite
7758-19-2

sodium chlorite

(1-tritylimidazol-4-yl)carboxaldehyde
33016-47-6

(1-tritylimidazol-4-yl)carboxaldehyde

1H-1-triphenylmethylimidazole-4-carboxylic acid
191103-80-7

1H-1-triphenylmethylimidazole-4-carboxylic acid

Conditions
ConditionsYield
With potassium dihydrogenphosphate In water91%
4-amino-1-benzylpiperidine
50541-93-0

4-amino-1-benzylpiperidine

(1-tritylimidazol-4-yl)carboxaldehyde
33016-47-6

(1-tritylimidazol-4-yl)carboxaldehyde

1-benzyl-N-[(1-trityl-1H-imidazol-4-yl)methyl]piperidin-4-amine
701300-00-7

1-benzyl-N-[(1-trityl-1H-imidazol-4-yl)methyl]piperidin-4-amine

Conditions
ConditionsYield
Stage #1: 4-amino-1-benzylpiperidine; (1-tritylimidazol-4-yl)carboxaldehyde With sodium tris(acetoxy)borohydride; acetic acid In dichloromethane at 20℃;
Stage #2: With sodium hydroxide In dichloromethane
90%
3,4-dimethyliodobenzene
31599-61-8

3,4-dimethyliodobenzene

(1-tritylimidazol-4-yl)carboxaldehyde
33016-47-6

(1-tritylimidazol-4-yl)carboxaldehyde

C31H28N2O

C31H28N2O

Conditions
ConditionsYield
Stage #1: 3,4-dimethyliodobenzene With isopropylmagnesium chloride In tetrahydrofuran at 12 - 15℃; for 3.33h;
Stage #2: (1-tritylimidazol-4-yl)carboxaldehyde In tetrahydrofuran at 15 - 25℃; for 3h;
89.9%
trimethyl 2-(tert-butoxycarbonylamino)phosphonoacetate
121056-95-9

trimethyl 2-(tert-butoxycarbonylamino)phosphonoacetate

(1-tritylimidazol-4-yl)carboxaldehyde
33016-47-6

(1-tritylimidazol-4-yl)carboxaldehyde

2-tert-butoxycarbonylamino-3-(1-trityl-1H-imidazol-4-yl)acrylic acid methyl ester

2-tert-butoxycarbonylamino-3-(1-trityl-1H-imidazol-4-yl)acrylic acid methyl ester

Conditions
ConditionsYield
With 1,8-diazabicyclo[5.4.0]undec-7-ene at 20℃; Horner-Wadsworth-Emmons reaction;89%
With N,N,N',N'-tetramethylguanidine In tetrahydrofuran at 0 - 20℃; for 21h;
Methyltriphenylphosphonium bromide
1779-49-3

Methyltriphenylphosphonium bromide

(1-tritylimidazol-4-yl)carboxaldehyde
33016-47-6

(1-tritylimidazol-4-yl)carboxaldehyde

4-ethenyl-1-(triphenylmethyl)-1H-imidazole
86803-29-4

4-ethenyl-1-(triphenylmethyl)-1H-imidazole

Conditions
ConditionsYield
Stage #1: Methyltriphenylphosphonium bromide With sodium hexamethyldisilazane In tetrahydrofuran at 0℃; for 0.5h;
Stage #2: (1-tritylimidazol-4-yl)carboxaldehyde In tetrahydrofuran at 0 - 20℃; for 3h;
86%
With sodium hydride In dimethyl sulfoxide at 70℃; for 4.5h;82%
With sodium hydride In tetrahydrofuran for 8h; Ambient temperature;81%
Stage #1: Methyltriphenylphosphonium bromide With potassium tert-butylate In tetrahydrofuran for 0.5h; Inert atmosphere;
Stage #2: (1-tritylimidazol-4-yl)carboxaldehyde In tetrahydrofuran at 20℃; for 2h; Wittig Olefination; Inert atmosphere;
66%
(2-tert-butoxy-2-oxoethyl)zinc(II) bromide
51656-70-3

(2-tert-butoxy-2-oxoethyl)zinc(II) bromide

(1-tritylimidazol-4-yl)carboxaldehyde
33016-47-6

(1-tritylimidazol-4-yl)carboxaldehyde

tert-butyl 3-hydroxy-3-(1-trityl-1H-imidazol-4-yl)propanoate

tert-butyl 3-hydroxy-3-(1-trityl-1H-imidazol-4-yl)propanoate

Conditions
ConditionsYield
Stage #1: 1-triphenylmethyl-5-imidazolecarboxaldehyde; tert-butyl bromozincacetate In tetrahydrofuran at 2 - 9℃; for 3.5h;
Stage #2: With hydrogenchloride In tetrahydrofuran; water at 20℃;
86%

33016-47-6Relevant articles and documents

Efficient molar-scale synthesis of 1-methyl-5-acylimidazole triflic acid salts

Chen, Bang-Chi,Skoumbourdis, Amanda P.,Sundeen, Joseph E.,Rovnyak, George C.,Traeger, Sarah C.

, p. 613 - 614 (2000)

A new process for the molar-scale preparation of 1-methyl-5-acylimidazole triflic acid salts was developed. The new process consists of: (i) regioselective 3N-tritylation of 5-acylimidazole to give 3-trityl-5-acylimidazoles, (ii) 1N-methylation of 3-trityl-5-acylimidazoles, and (iii) hydrolysis of the resulting quaternary ammonium salts to afford 1-methyl-5-acylimidazole triflic acid salts. This process is highly efficient, affording 1-methyl-5-acylimidazole triflic acid salts in 86-88% overall yield in three steps without chromatographic separation of products.

Expedient synthesis of N1-tritylimidazole-4-carboxaldehyde

Jetter, Michele C.,Boyd, Robert E.,Reitz, Allen B.

, p. 709 - 710 (1996)

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PURIFIED CRYSTALLINE DETOMIDINE HYDROCHLORIDE MONOHYDRATE, ANHYDRATE AND FREE BASE WITH LOW AMOUNTS OF ISO-DETOMIDINE AND OTHER IMPURITIES BY RECRYSTALLISATION IN WATER

-

Page/Page column 26; 27, (2020/02/14)

The present disclosure relates to crystalline detomidine hydrochloride monohydrate, anhydrous detomidine hydrochloride and detomidine free base (4-[(2,3-dimethylphenyl)methyl]-1H-lmidazole ), purified by recrystallisation in water, with a low amount (total amount of impurities is not more than 0.1% area relative to detomidine based on HPLC, UV detection at 220 nm) of the impurities iso-detomidine (4-[(3,4-dimethylphenyl)methyl]-1H-lmidazole ), iso-impurity A (((RS)-(3,4-dimethylphenyl)(1H-imidazol-4-yl)methanol)), impurity A ((RS)-(2,3-dimethylphenyl)(1H-imidazol-4-yl)methanol), "ketone impurity" (2,3-dimethylphenyl)(1H-imidazol-4-yl) methanone, impurity B ((RS)-(1-benzyl-1H-imidazol-5-yl)(2, 3-dimethyl phenyl) methanol) and impurity C (4-[(2,3-dimethylcyclohexyl)methyl]-1H-imidazole). Also disclosed are processes for recrystallising detomidine hydrochloride monohydrate from commercially available anhydrous detomidine hydrochloride in water, pharmaceutical compositions comprising detomidine hydrochloride in purified form for use as an analgesic in methods of treating human subjects, a process for validating a batch of detomidine hydrochloride drug substance by determining the content of impurities iso-detomidine and iso- impurity A by HPLC, as well as XRPD, DSC and TGA data of crystalline detomidine free base.

Concise Synthesis of Anserine: Efficient Solvent Tuning in Asymmetric Hydrogenation Reaction

Yamashita, Megumi,Shimizu, Keita,Koizumi, Yasuaki,Wakimoto, Toshiyuki,Hamashima, Yoshitaka,Asakawa, Tomohiro,Inai, Makoto,Kan, Toshiyuki

supporting information, p. 2734 - 2736 (2016/11/30)

A concise synthesis of anserine and related compounds was accomplished by Et-DuPhos-Rh-catalyzed asymmetric hydrogenation of dehydrohistidine derivatives in 2,2,2-trifluoroethanol, which played a key role in improving the yield and selectivity.

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