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

HRID 1440568Notes

Reaction equation

HRID 1440568 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].[OH-].[NH4+].[CH:17](=O)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.[NH:25]1[C:29]2[CH:30]=[CH:31][CH:32]=[CH:33][C:28]=2[N:27]=[N:26]1>C1(C)C=CC=CC=1>[N:25]1([CH:17]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=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:29]2[CH:30]=[CH:31][CH:32]=[CH:33][C:28]=2[N:27]=[N:26]1

Participants

6

Reactant 4

HCID 240BenzaldehydeHCID 14923Ammonium HydroxideHCID 186302662-Chloro-6-trimethylsilylbenzamideHCID 178418385HCID 178418385, compound

Product 1

HCID 54455808N-(1H-Benzotriazol-1-ylphenylmethyl)-2-chloro-6-(trimethylsilyl)benzamideYield 11.5%

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-89f5f2d9390a42f8a5b7e639375e14bf
Source dataset
uspto-grants-1996_03
Patent number
US05498630

Reaction notes

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