Chloroform → 2-Amino-5-chloro-N-(2-chlorophenyl)benzamide

HRID 467880Notes

Reaction equation

HRID 467880 reaction equation
[NH2:1][C:2]1[CH:10]=[CH:9][C:8]([Cl:11])=[CH:7][C:3]=1[C:4]([OH:6])=O.O=S(Cl)Cl.[Cl:16][C:17]1[CH:23]=[CH:22][CH:21]=[CH:20][C:18]=1[NH2:19].C(Cl)(Cl)Cl>C1C=CC=CC=1>[NH2:1][C:2]1[CH:10]=[CH:9][C:8]([Cl:11])=[CH:7][C:3]=1[C:4]([NH:19][C:18]1[CH:20]=[CH:21][CH:22]=[CH:23][C:17]=1[Cl:16])=[O:6]

Participants

6

Reactant 4

HCID 6212ChloroformHCID 72402-ChloroanilineHCID 124762-Amino-5-chlorobenzoic acidHCID 24386Thionyl Chloride

Product 1

HCID 167817822-Amino-5-chloro-N-(2-chlorophenyl)benzamideYield 52.3%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

Prepared according to Procedure A using 2-amino-5-chlorobenzoic acid (2.0 g, 11.7 mmol) and SOCl2 (2.2 mL, 29.2 mmol) in benzene (50 mL), followed by 2-chloroaniline (2.5 mL, 23.3 mmol) and CHCl3 (50 mL). The product was purified by recrystallization from MeOH to provide 1.72 g of a dark yellow solid (52%). 1H NMR (CDCl3) δ: 8.37 (dd, J=1.5, 8.3 Hz, 1H); 8.22 (br s, 1H); 7.48 (d, J=2.3 Hz, 1H); 7.42 (dd, J=1.5, 8.1 Hz, 1H); 7.31 (dt, J=1.4, 7.8 Hz, 1H); 7.22 (dd, J=2.4, 8.8 Hz, 1H); 7.09 (dt, J=1.5, 7.7 Hz, 1H); 6.67 (d, J=8.8 Hz, 1H); 5.56 (br s, 2H).

Workup

  1. customPrepared
  2. customThe product was purified by recrystallization from MeOH

Sources & evidence

ORD record
ord-84b5a11f34184736978c48587343a527
Source dataset
uspto-grants-2014_01
Patent number
US08623881B2

Reaction notes

Loading…