4-Chlorobenzylamine hydrochloride → HCID 178512103, compound

HRID 636686Notes

Reaction equation

HRID 636686 reaction equation
[NH:1]([C:4]1[CH:5]=[C:6]([C:10]([F:13])([F:12])[F:11])[CH:7]=[CH:8][CH:9]=1)[C:2]#[N:3].Cl.[Cl:15][C:16]1[CH:23]=[CH:22][C:19]([CH2:20][NH2:21])=[CH:18][CH:17]=1>ClCCl>[Cl:15][C:16]1[CH:23]=[CH:22][C:19]([CH2:20][NH:21][C:2]([NH:1][C:4]2[CH:9]=[CH:8][CH:7]=[C:6]([C:10]([F:11])([F:12])[F:13])[CH:5]=2)=[NH:3])=[CH:18][CH:17]=1

Participants

4

Reactant 2

HCID 4584434-Chlorobenzylamine hydrochlorideHCID 110741023-(Trifluoromethyl)phenylcyanamide

Product 1

HCID 178512103HCID 178512103, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
150 °C

Procedure

A mixture of 3-cyanamidobenzotrifluoride (1.20 g, 6.45 mmol) and 4-chlorobenzylamine hydrochloride (1.26 g, 7.09 mmol) was stirred at 150° C. for 40 h. Dichloromethane (100 ml) was added and the mixture was washed with saturated aqueous sodium hydrogen carbonate (100 ml). The organic phase was purified by chromatography using silica gel and a mixture of methanol (10%) and dichloromethane as eluent. The product was isolated as the free base. Yield 1.05 g, 50%. M.p. 103-105° C.

Workup

  1. washthe mixture was washed with saturated aqueous sodium hydrogen carbonate (100 ml)
  2. customThe organic phase was purified by chromatography
  3. additiona mixture of methanol (10%) and dichloromethane as eluent
  4. customThe product was isolated as the free base

Sources & evidence

ORD record
ord-258a3a7bc4e844d4afbbece4735408c0
Source dataset
uspto-grants-2001_02
Patent number
US06194447B1

Reaction notes

Loading…