Methanol → Benzoic acid, 3-(aminosulfonyl)-, methyl ester

HRID 331188

반응식

HRID 331188 반응식
[NH2:1][S:2]([C:5]1[CH:6]=[C:7]([CH:11]=[CH:12][CH:13]=1)[C:8]([OH:10])=[O:9])(=[O:4])=[O:3].S(Cl)(Cl)=O.[CH3:18]O>>[NH2:1][S:2]([C:5]1[CH:6]=[C:7]([CH:11]=[CH:12][CH:13]=1)[C:8]([O:10][CH3:18])=[O:9])(=[O:3])=[O:4]

참가 물질

4

반응물 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 2293523-Sulfamoylbenzoic acid

생성물 1

HCID 108836Benzoic acid, 3-(aminosulfonyl)-, methyl ester수율 73%

실험 절차

To a solution of 3-(aminosulfonyl)benzoic acid (22 g, 0.109 mol) in MeOH (250 ml) is added thionyl chloride (25 ml, 0.328 mol) and the mixture is refluxed for 16 h. The solvent is removed and the residue is diluted with EtOAc (200 ml), washed with a 10% solution of sodium bicarbonate, water and brine. The solvent was removed under vacuum to afford 17 g (73%) of the title compound as a solid. 1H NMR (DMSO-d6) δ 8.39 (t, J=1.5 Hz, 1H), 8.16-8.13 (m, 1H), 8.09-8.05 (m, 1H), 7.76 (t, J=7.9 Hz, 1H), 7.53 (s, 2H), 3.90 (s, 3H). HPLC (max plot) 99%; Rt 1.49 min. LC/MS: (ES+):215.9, (ES−):214.1.

후처리

  1. temperaturethe mixture is refluxed for 16 h
  2. customThe solvent is removed
  3. additionthe residue is diluted with EtOAc (200 ml)
  4. washwashed with a 10% solution of sodium bicarbonate, water and brine
  5. customThe solvent was removed under vacuum

출처 및 근거

ORD 기록
ord-906813f66a2b49e89bf0d203116b5627
출처 데이터셋
uspto-grants-2014_11
특허 번호
US08877757B2

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