Water → methyl 5-[(2-nitrophenyl)sulfonyl]-5,6-dihydro-4H-thieno[2,3-c]pyrrole-2-carboxylate

HRID 468680

반응식

HRID 468680 반응식
Cl[CH2:2][C:3]1[CH:4]=[C:5]([C:10]([O:12][CH3:13])=[O:11])[S:6][C:7]=1[CH2:8]Cl.[N+:14]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[S:23]([NH2:26])(=[O:25])=[O:24])([O-:16])=[O:15].C(=O)([O-])[O-].[K+].[K+].O>CC(C)=O>[N+:14]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[S:23]([N:26]1[CH2:2][C:3]2[CH:4]=[C:5]([C:10]([O:12][CH3:13])=[O:11])[S:6][C:7]=2[CH2:8]1)(=[O:24])=[O:25])([O-:16])=[O:15]

참가 물질

6

반응물 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 1385102-NitrobenzenesulfonamideHCID 11096691Methyl 4,5-bis(chloromethyl)thiophene-2-carboxylate

생성물 1

HCID 58157834methyl 5-[(2-nitrophenyl)sulfonyl]-5,6-dihydro-4H-thieno[2,3-c]pyrrole-2-carboxylate수율 53%

시약·촉매·용매 1

HCID 180Acetone용매

실험 절차

To a solution of methyl 4,5-bis(chloromethyl)thiophene-2-carboxylate (4.106 g, 17.17 mmol) and 2-nitrobenzenesulfonamide (3.825 g, 18.92 mmol) in acetone (40 mL) was added 2.5 M of potassium carbonate in water (20 mL, 50 mmol). The resulting biphasic mixture was stirred at room temperature for 1 hour then further heated at 45° C. overnight resulting in formation of precipitate. The reaction mixture was cooled to room temperature and the precipitate was collected by vacuum filtration. The solid obtained was washed with water followed by cold methanol and dried under vacuum to afford an off white solid (3.352 g, 53%). LCMS (FA) ES+ 369; 1H NMR (400 MHz, DMSO) δ 8.02 (ddd, J=7.8, 4.9, 1.4 Hz, 2H), 7.90 (td, J=7.7, 1.5 Hz, 1H), 7.84 (td, J=7.7, 1.4 Hz, 1H), 7.63 (s, 1H), 4.79 (t, J=2.9 Hz, 2H), 4.60 (t, J=2.9 Hz, 2H), 3.80 (s, 3H).

후처리

  1. temperaturethen further heated at 45° C. overnight
  2. customresulting in formation of precipitate
  3. temperatureThe reaction mixture was cooled to room temperature
  4. filtrationthe precipitate was collected by vacuum filtration
  5. customThe solid obtained
  6. washwas washed with water
  7. customdried under vacuum

출처 및 근거

ORD 기록
ord-35685b8365cd4f66824334632e3f642e
출처 데이터셋
uspto-grants-2014_01
특허 번호
US08624040B2

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