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Hydrochloric Acid → 3-(Toluene-2-sulfonylamino)-thiophene-2-carboxylic acid

HRID 1015613
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HRID 1015613 반응식
C[O:2][C:3]([C:5]1[S:6][CH:7]=[CH:8][C:9]=1[N:10](S(C1C(C)=CC=CC=1)(=O)=O)[S:11]([C:14]1[C:15]([CH3:20])=[CH:16][CH:17]=[CH:18][CH:19]=1)(=[O:13])=[O:12])=[O:4].[OH-].[Na+].Cl>O1CCOCC1.CO.O>[C:15]1([CH3:20])[C:14]([S:11]([NH:10][C:9]2[CH:8]=[CH:7][S:6][C:5]=2[C:3]([OH:4])=[O:2])(=[O:13])=[O:12])=[CH:19][CH:18]=[CH:17][CH:16]=1
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참가 물질

5

반응물 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 672990783-(bis-(Toluene-2-sulfonyl)-amino)-thiophene-2-carboxylic acid methyl ester

생성물 1

HCID 224961893-(Toluene-2-sulfonylamino)-thiophene-2-carboxylic acid수율 99%

시약·촉매·용매 1

HCID 22592949Dioxane methanol water용매

반응 조건

온도
85 °C

실험 절차

To a stirred mixture of 3-(bis-(Toluene-2-sulfonyl)-amino)-thiophene-2-carboxylic acid methyl ester (2.5 g, 5.35 mmol) in 1,4-dioxane/MeOH/water (3:1:1; 62.5 mL) was added aq. 1 N NaOH solution (16.05 mL, 16.05 mmol, 3.0 eq) and heated at 85° C. for 3.5 h and it was then cooled to rt. To the reaction mixture was added 1.2 N HCl (16.0 mL), extracted with CHCl3 (3×30 mL), washed with brine and dried. Evaporation of the solvent gave 3-(Toluene-2-sulfonylamino)-thiophene-2-carboxylic acid (1.5 g, 99%) as a white solid. 1H NMR (DMSO-d6, 300 MHz) 7.94 (dd, J=7.9 Hz, 1.3 Hz, 1H), 7.76 (d, J=5.5 Hz, 1H), 7.55 (dt, J=7.5 Hz, 1.3 Hz, 1H), 7.42-7.37 (m, 2H), 7.1 (d, J=5.5 Hz, 1H), 2.57 (s, 3H).

후처리

  1. temperatureit was then cooled to rt
  2. extractionextracted with CHCl3 (3×30 mL)
  3. washwashed with brine
  4. customdried
  5. customEvaporation of the solvent

출처 및 근거

ORD 기록
ord-36c3f3c12f374338afecb1c44dfe7269
출처 데이터셋
uspto-grants-2011_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07985769B2

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