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

HRID 655615

反応式

HRID 655615 の反応式
[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]

参加物

4

反応物 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 2293523-Sulfamoylbenzoic acid

生成物 1

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

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-36490e8a8c754e9fa56472c859f1d6bd
出典データセット
uspto-grants-2011_12
特許番号
US08071597B2

関連ノート

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