1,1-Dichloroethane → HCID 19759896, compound
Reaction equation
C(N1C=CN=C1)([N:3]1C=CN=C1)=O.[CH3:13][C:14]1([C:24]([OH:26])=O)[S:21](=[O:23])(=[O:22])[C:17]2[S:18][CH:19]=[CH:20][C:16]=2[CH2:15]1.ClC(Cl)C>>[CH3:13][C:14]1([C:24]([NH2:3])=[O:26])[S:21](=[O:23])(=[O:22])[C:17]2[S:18][CH:19]=[CH:20][C:16]=2[CH2:15]1Participants
Procedure
Carbonyldiimidazole (13.3 g, 82.0 mmol) was added to a solution of 2,3-dihydro-2-methylthieno[2,3-b]thiophene-2-carboxylic acid-1,1-dioxide (12.7 g, 54.7 mmol) in dry, degassed DMF (200 mL). The reaction was stirred under N2 until an aliquot quenched with methanol showed no more starting material by tlc (about 1 h). An excess of a saturated solution of NH3 (g) in CHCl3 was added and the reaction stirred 1.5 h. The reaction was diluted with water and extracted with ethyl acetate 3X. The combined organic extracts were washed with brine and dried over MgSO4, filtered, and the solvent removed in vacuo to give a semi-solid. This semi-solid was treated with dichloroethane, cooled in the freezer, and filtered to give the title compound (6.69 g, 53%). 1H NMR (300 MHz,DMSO-d6) 1.70(s,3H), 3.00(d, 1H), 3.85(d,1H), 7.10(d,1H), 7.63(bs,1H exch.), 7.69(bs,1 H, exch.), 8.05(d,1H).
Workup
- customin dry
- customdegassed DMF (200 mL)
- customquenched with methanol
- customby tlc (about 1 h)
- additionAn excess of a saturated solution of NH3 (g) in CHCl3 was added
- stirringthe reaction stirred 1.5 h
- additionThe reaction was diluted with water
- extractionextracted with ethyl acetate 3X
- washThe combined organic extracts were washed with brine
- dry with materialdried over MgSO4
- filtrationfiltered
- customthe solvent removed in vacuo
- customto give a semi-solid
- temperaturecooled in the freezer
- filtrationfiltered
Sources & evidence
- ORD record
- ord-99982dc7e9544bea8f188a917756e925
- Source dataset
- uspto-grants-1993_06
- Patent number
- US05216020
Reaction notes
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