Chloroform → 2-amino-6-chloro-N-(2-chlorophenyl)benzamide

HRID 1058868Notes

Reaction equation

HRID 1058868 reaction equation
[NH2:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]([Cl:11])[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][CH:8]=[C:7]([Cl:11])[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 750712-Amino-6-chlorobenzoic acid

Product 1

HCID 223165862-amino-6-chloro-N-(2-chlorophenyl)benzamideYield 26%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

Prepared according to Procedure A using 2-amino-6-chlorobenzoic acid (2.5 g, 14.6 mmol) and SOCl2 (2.7 mL, 36.4 mmol) in benzene (75 mL), followed by 2-chloroaniline (3.1 mL, 29.1 mmol) and CHCl3 (75 mL). The product chromatographed in CH2Cl2 to provide 1.05 g of a yellow orange solid (26%). 1H NMR (CDCl3) δ: 8.54 (d, J=8.1 Hz, 1H); 8.30 (br s, 1H); 7.41 (dd, J=1.5, 8.0 Hz, 1H); 7.33 (t, J=7.8 Hz, 1H); 7.10 (t, J=8.1 Hz, 1H); 7.09 (dt, J=1.6, 7.8 Hz, 1H); 6.78 (dd, J=0.4, 7.9 Hz, 1H); 6.63 (dd, J=0.9, 8.2 Hz, 1H); 4.69 (br s, 2H). MS (ES): m/z 303.0 (M+22), 281.0 (M+).

Workup

  1. customPrepared
  2. customThe product chromatographed in CH2Cl2

Sources & evidence

ORD record
ord-aab00f42ec474a61b9ec301103c2a18b
Source dataset
uspto-grants-2003_02
Patent number
US06518277B1

Reaction notes

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