Chloroform → 2-amino-5-bromo-N-(2-chlorophenyl)benzamide

HRID 392230

Reaction equation

HRID 392230 reaction equation
[NH2:1][C:2]1[CH:10]=[CH:9][C:8]([Br: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]([Br: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 24386Thionyl ChlorideHCID 798582-Amino-5-bromobenzoic acid

Product 1

HCID 223165482-amino-5-bromo-N-(2-chlorophenyl)benzamideYield 20%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

Prepared according to Procedure A using 2-amino-5-bromobenzoic acid (5.0 g, 23.1 mmol) and SOCl2 (7.0 mL, 95.9 mmol) in benzene (50 mL), followed by 2-chloroaniline (7.3 mL, 69.3 mmol) and CHCl3 (50 mL). The product was purified by two chromatographies in CH2Cl2 to provide 1.48 g of a yellow orange solid (20%). 1H NMR (CDCl3) δ: 8.36 (dd, J=1.2, 8.2 Hz, 1H); 8.20 (br s, 1H); 7.62 (d, J=2.1 Hz, 1H); 7.42 (dd, J=1.3, 8.0 Hz, 1H); 7.34 (dd, J=2.2, 8.8 Hz, 1H); 7.28-7.33 (m, 1H); 7.09 (dt, J=1.4, 7.7 Hz, 1H); 6.62 (d, J=8.7 Hz, 1H); 5.57 (br s, 2H).

Workup

  1. customPrepared
  2. customThe product was purified by two chromatographies in CH2Cl2

Sources & evidence

ORD record
ord-2072c7bd91174bb387a1d0eafc07c515
Source dataset
uspto-grants-2004_10
Patent number
US06800620B2

Linked notes

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