Chloroform → 2-Amino-N-biphenyl-2-yl-6-chlorobenzamide

HRID 433233Notes

Reaction equation

HRID 433233 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.[NH2:16][C:17]1(N)[CH2:22][CH:21]=[CH:20][CH:19]=[C:18]1[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.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:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1)=[O:6]

Participants

6

Reactant 4

HCID 6212ChloroformHCID 24386Thionyl ChlorideHCID 750712-Amino-6-chlorobenzoic acidHCID 667830042-Aminobiphenylamine

Product 1

HCID 223165622-Amino-N-biphenyl-2-yl-6-chlorobenzamideYield 57.2%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

Prepared according to Procedure A using 2-amino-6-chlorobenzoic acid (2.0 g, 11.7 mmol) and SOCl2 (2.1 mL, 29.3 mmol) in benzene (60 mL), followed by 2-aminobiphenylamine (4.15 g, 24.5 mmol) and CHCl3 (60 mL). The product was chromatographed in CH2Cl2 to provide 2.16 g of a foamy dark-amber residue (57%). 1H NMR (CDCl3) δ: 8.48 (d, J=8.2 Hz, 1H); 7.79 (br s, 1H); 7.34-7.46 (m, 6H); 7.20-7.30 (m, 2H); 7.00 (t, J=8.1 Hz, 1H); 6.63 (dd, J=0.6, 7.9 Hz, 1H); 6.54 (d, J=8.3 Hz, 1H); 4.58 (br s, 2H). MS (ES): m/z 323.1 (M+).

Workup

  1. customPrepared
  2. customThe product was chromatographed in CH2Cl2

Sources & evidence

ORD record
ord-f9b31b164674401b94e0c853816d27a7
Source dataset
uspto-grants-2003_12
Patent number
US06667300B2

Reaction notes

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