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

HRID 2265198노트

반응식

HRID 2265198 반응식
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

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 962Water용매HCID 8028Tetrahydrofuran용매

실험 절차

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).

후처리

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

출처 및 근거

ORD 기록
ord-421a8e52c3784cd28667d3504dcade89
출처 데이터셋
uspto-grants-2010_12
특허 번호
US07855292B2

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