Chloroform → 2-amino-N-(2-chlorophenyl)-4,5-dimethoxybenzamide

HRID 392229Notes

Reaction equation

HRID 392229 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([NH2:14])[C:6](=[CH:10][C:11]=1[O:12][CH3:13])[C:7]([OH:9])=O.O=S(Cl)Cl.[Cl:19][C:20]1[CH:26]=[CH:25][CH:24]=[CH:23][C:21]=1[NH2:22].C(Cl)(Cl)Cl>C1C=CC=CC=1>[NH2:14][C:5]1[CH:4]=[C:3]([O:2][CH3:1])[C:11]([O:12][CH3:13])=[CH:10][C:6]=1[C:7]([NH:22][C:21]1[CH:23]=[CH:24][CH:25]=[CH:26][C:20]=1[Cl:19])=[O:9]

Participants

6

Reactant 4

HCID 6212ChloroformHCID 72402-ChloroanilineHCID 24386Thionyl ChlorideHCID 797364,5-Dimethoxyanthranilic acid

Product 1

HCID 141271432-amino-N-(2-chlorophenyl)-4,5-dimethoxybenzamideYield 55.2%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

Prepared according to Procedure A using 4,5-dimethoxyanthranilic acid (5.0 g, 25.4 mmol) and SOCl2 (5.5 mL, 76.1 mmol) in benzene (100 mL), followed by 2-chloroaniline (6.7 mL, 63.5 mmol) and CHCl3 (75 mL). The product was washed with aqueous NaHCO3 (2×25 mL) and HCl (0.5 M, 75 mL) and purified by chromatography in CH2Cl2 to provide 4.3 g of a brown foam (55%). 1H NMR (CDCl3) δ: 8.42 (dd, J=1.5, 8.3 Hz, 1H); 8.32 (br s, 1H); 7.40 (dd, J=1.4, 8.0 Hz, 1H); 7.31 (dt, J=1.4, 7.9 Hz, 1H); 7.05 (dt, J=1.5, 7.7 Hz, 1H); 7.03 (s, 1H); 6.24 (s, 1H); 3.88 (s, 3H); 3.87 (s, 3H). MS (ES): m/z 307.0 (M+).

Workup

  1. customPrepared
  2. washThe product was washed with aqueous NaHCO3 (2×25 mL) and HCl (0.5 M, 75 mL)
  3. custompurified by chromatography in CH2Cl2

Sources & evidence

ORD record
ord-5c36cd6ed6ef4a8fae4768cf9344c841
Source dataset
uspto-grants-2004_10
Patent number
US06800620B2

Reaction notes

Loading…