Hydrochloric Acid → 2-(Benzo[1,2,5]thiadiazole-4-sulfonylamino)-4,5-dichlorobenzoic acid

HRID 2265198ノート

反応式

HRID 2265198 の反応式
C[O:2][C:3](=[O:25])[C:4]1[CH:9]=[C:8]([Cl:10])[C:7]([Cl:11])=[CH:6][C:5]=1[NH:12][S:13]([C:16]1[C:21]2=[N:22][S:23][N:24]=[C:20]2[CH:19]=[CH:18][CH:17]=1)(=[O:15])=[O:14].O[Li].O.Cl>C1COCC1.O>[N:24]1[S:23][N:22]=[C:21]2[C:16]([S:13]([NH:12][C:5]3[CH:6]=[C:7]([Cl:11])[C:8]([Cl:10])=[CH:9][C:4]=3[C:3]([OH:25])=[O:2])(=[O:15])=[O:14])=[CH:17][CH:18]=[CH:19][C:20]=12

参加物

6

反応物 3

HCID 313Hydrochloric AcidHCID 168937Lithium hydroxide, monohydrateHCID 687705432-(Benzo[1,2,5]thiadiazole-4-sulfonylamino)-4,5-dichloro-benzoic acid methyl ester

生成物 1

HCID 160907562-(Benzo[1,2,5]thiadiazole-4-sulfonylamino)-4,5-dichlorobenzoic acid収率 88%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution of 2-(benzo[1,2,5]thiadiazole-4-sulfonylamino)-4,5-dichloro-benzoic acid methyl ester (0.95 g, 2.3 mmol) in THF (21 mL) and water (7 mL) was added LiOH.H2O (0.38 g, 9.1 mmol). The biphasic mixture was stirred overnight at rt. The mixture was acidified with conc. HCl and extracted with DCM (3×). The combined organic layers were dried (MgSO4) and concentrated to provide 0.80 g (88%) of the pure acid as a white solid. 1H NMR (500 MHz, CDCl3): 11.07 (s, 1H), 8.41 (dd, J=7.0, 1.0, 1H), 8.27 (dd, J=8.8, 1.0, 1H), 8.01 (s, 1H), 7.94 (s, 1H), 7.75 (dd, J=8.8, 7.0, 1H).

後処理

  1. extractionextracted with DCM (3×)
  2. dry with materialThe combined organic layers were dried (MgSO4)
  3. concentrationconcentrated

出典と根拠

ORDレコード
ord-421a8e52c3784cd28667d3504dcade89
出典データセット
uspto-grants-2010_12
特許番号
US07855292B2

反応ノート

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