Chloroform → 2-amino-N-(2-chlorophenyl)-5-hydroxybenzamide

HRID 452898

반응식

HRID 452898 반응식
[NH2:1][C:2]1[CH:10]=[CH:9][C:8]([OH: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]([OH: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]

참가 물질

6

반응물 4

HCID 6212ChloroformHCID 72402-ChloroanilineHCID 24386Thionyl ChlorideHCID 1645925-Hydroxyanthranilic acid

생성물 1

HCID 223165642-amino-N-(2-chlorophenyl)-5-hydroxybenzamide수율 12%

시약·촉매·용매 1

HCID 241Benzene용매

실험 절차

Prepared according to Procedure A using 2-amino-5-hydroxybenzoic acid (5.0 g, 32.7 mmol) and SOCl2 (6.0 mL, 81.6 mmol) in benzene (150 mL), followed by 2-chloroaniline (6.9 mL, 65.4 mmol) and CHCl3 (150 mL). The product was purified by two chromatographies in MeOH/CH2Cl2 to provide 990 mg of a brown solid (12%). 1H NMR (MeOH-d4) δ: 7.92 (dd, J=1.6, 8.1 Hz, 1H); 7.48 (dd, J=1.5, 7.7 Hz, 1H); 7.34 (dt, J=1.5, 7.7 Hz, 1H); 7.20 (dt, J=1.7, 7.7 Hz, 1H); 7.16 (d, J=2.7 Hz, 1H); 6.83 (dd, J=2.7, 8.7 Hz, 1H); 6.76 (d, J=8.7 Hz, 1H); [6.24 (br s, 2H)). MS (ES): m/z 263.0 (M+).

후처리

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

출처 및 근거

ORD 기록
ord-1526ee7e5dfa45018a871f5f75d40450
출처 데이터셋
uspto-grants-2013_07
특허 번호
US08492389B2

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