3-(Trifluoromethyl)aniline → HCID 10269420, compound

HRID 2228855Notes

Reaction equation

HRID 2228855 reaction equation
Br[CH2:2][CH2:3][NH:4][C:5]1[CH:15]=[CH:14][CH:13]=[CH:12][C:6]=1[C:7]([O:9][CH2:10][CH3:11])=[O:8].[NH2:16][C:17]1[CH:18]=[C:19]([C:23]([F:26])([F:25])[F:24])[CH:20]=[CH:21][CH:22]=1.C(N(CC)CC)C>O>[F:24][C:23]([F:25])([F:26])[C:19]1[CH:18]=[C:17]([NH:16][CH2:2][CH2:3][NH:4][C:5]2[CH:15]=[CH:14][CH:13]=[CH:12][C:6]=2[C:7]([O:9][CH2:10][CH3:11])=[O:8])[CH:22]=[CH:21][CH:20]=1

Participants

5

Reactant 3

HCID 73753-(Trifluoromethyl)anilineHCID 8471TriethylamineHCID 23434247HCID 23434247, compound

Product 1

HCID 10269420HCID 10269420, compoundYield 37.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
110 °C

Procedure

Ethyl N-(2-bromoethyl)aminobenzoate (3.3 g, 12 mmol), 3-aminobenzotriflouride (1.5 mL, 12 mmol) and triethylamine (2 mL, 14 mmol) were mixed in dimethyltormamide (25 mL). The reaction mixture was heated at 110° C. for five hours. The cooled reaction mixture was poured into water and extracted with diethyl ether. Purification by column chromatography on silica gel using dichloromethane as eluent gave 1.6 g of the desired material.

Workup

  1. customThe cooled reaction mixture
  2. extractionextracted with diethyl ether
  3. customPurification by column chromatography on silica gel

Sources & evidence

ORD record
ord-58ec74f780a74474b0d050b5d0da89b1
Source dataset
uspto-grants-2002_07
Patent number
US06417393B1

Reaction notes

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