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

HRID 468680

Reaction equation

HRID 468680 reaction equation
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]

Participants

6

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-35685b8365cd4f66824334632e3f642e
Source dataset
uspto-grants-2014_01
Patent number
US08624040B2

Linked notes

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