Chloroform → 2-amino-3-chloro-N-(2-chlorophenyl)benzamide

HRID 241894

Reaction equation

HRID 241894 reaction equation
[NH2:1][C:2]1[C:10]([Cl:11])=[CH:9][CH:8]=[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[C:10]([Cl:11])=[CH:9][CH:8]=[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 808072-Amino-3-chlorobenzoic acid

Product 1

HCID 223165852-amino-3-chloro-N-(2-chlorophenyl)benzamideYield 78.8%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

Prepared according to Procedure A using 2-amino-3-chlorobenzoic acid (1.0 g, 5.82 mmol) and SOCl2 (1.1 mL, 14.6 mmol) in benzene (25 mL), followed by 2-chloroaniline (1.2 mL, 11.7 mmol) and CHCl3 (25 mL). The product was recrystallized from MeOH to provide 1.29 g of a yellow solid (78%). 1H NMR (CDCl3) δ: 8.43 (dd, J=1.4, 8.3 Hz, 1H); 8.30 (br s, 1H); 7.47 (dd, J=1.1, 8.0 Hz, 1H); 7.42 (d, J=8.0 Hz, 2H); 7.33 (dt, J=1.4, 7.9 Hz, 1H); 7.09 (dt, J=1.5, 7.7 Hz, 1H); 6.68 (t, J=7.9 Hz, 1H); 6.13 (br s, 2H). MS (ES): m/z 281.0 (M+).

Workup

  1. customPrepared
  2. customThe product was recrystallized from MeOH

Sources & evidence

ORD record
ord-bb880e11877741528538b6ef448ff40c
Source dataset
uspto-grants-2014_02
Patent number
US08653077B2

Linked notes

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