Benzaldehyde → N-(1H-Benzotriazol-1-ylphenylmethyl)-2-chloro-6-(trimethylsilyl)benzamide

HRID 1458091Notes

Reaction equation

HRID 1458091 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]([Si:11]([CH3:14])([CH3:13])[CH3:12])[C:3]=1[C:4]([NH2:6])=[O:5].Cl[C:16]1[CH:24]=[CH:23][CH:22]=[C:21]([Si](C)(C)C)[C:17]=1[C:18](Cl)=O.[OH-].[NH4+].C(=O)C1C=CC=CC=1.[NH:39]1[C:43]2[CH:44]=[CH:45][CH:46]=[CH:47][C:42]=2[N:41]=[N:40]1>C1(C)C=CC=CC=1>[N:39]1([CH:18]([C:17]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:16]=2)[NH:6][C:4](=[O:5])[C:3]2[C:7]([Si:11]([CH3:14])([CH3:13])[CH3:12])=[CH:8][CH:9]=[CH:10][C:2]=2[Cl:1])[C:43]2[CH:44]=[CH:45][CH:46]=[CH:47][C:42]=2[N:41]=[N:40]1

Participants

7

Reactant 5

HCID 240BenzaldehydeHCID 14923Ammonium HydroxideHCID 151835572-Chloro-6-(trimethylsilyl)benzoyl chlorideHCID 186302662-Chloro-6-trimethylsilylbenzamideHCID 178418385HCID 178418385, compound

Product 1

HCID 54455808N-(1H-Benzotriazol-1-ylphenylmethyl)-2-chloro-6-(trimethylsilyl)benzamide

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 2-chloro-6-trimethylsilylbenzamide (2.27 g, 10 mmol), which may be readily prepared by the reaction of the compound of Example b and ammonium hydroxide, benzaldehyde (1.1 g, 10 mmol), and benzotriazole (1.2 g, 10 mmol) was refluxed 5 days in toluene utilizing a Dean-Stark trap to remove water. The solvent was removed to yield an oil which crystallizes. Recrystallization from ethyl acetate yielded 0.5 g of the title compound. m.p. 184°-186° C.

Workup

  1. customto remove water
  2. customThe solvent was removed
  3. customto yield an oil which
  4. customcrystallizes
  5. customRecrystallization from ethyl acetate

Sources & evidence

ORD record
ord-6a702974cb5f4a8db96665e9c6d3bf21
Source dataset
uspto-grants-1998_12
Patent number
US05849723

Reaction notes

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