1,1-Dichloroethane → HCID 19759896、化合物

反応式

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]1

参加物

反応物 3

HCID 63651,1-Dichloroethane

HCID 682631,1'-Carbonyldiimidazole

HCID 19759891HCID 19759891、化合物

生成物 1

HCID 19759896HCID 19759896、化合物収率 53%

実験手順

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).