1,2-Dichloroethane → 5-Nitrothiophene-2-carboxamide

반응식

[N+:1]([C:4]1[S:8][C:7]([C:9]([OH:11])=O)=[CH:6][CH:5]=1)([O-:3])=[O:2].[NH4+].[Cl-].C1C=CC2N(O)N=[N:20]C=2C=1.C(Cl)CCl.CCN(C(C)C)C(C)C>CN(C=O)C>[N+:1]([C:4]1[S:8][C:7]([C:9]([NH2:20])=[O:11])=[CH:6][CH:5]=1)([O-:3])=[O:2]

참가 물질

반응물 5

HCID 111,2-Dichloroethane

HCID 25517Ammonium Chloride

HCID 757711-Hydroxybenzotriazole

HCID 805915-Nitro-2-thenoic acid

HCID 81531Diisopropylethylamine

생성물 1

HCID 3147105-Nitrothiophene-2-carboxamide

시약·촉매·용매 1

실험 절차

5-Nitro-2-thiophenecarboxylic acid (7.50 g, 43.3 mmol), NH4Cl (6.95 g, 130 mmol), HOBT (8.62 g, 56.3 mmol), and EDC (12.46 g, 65.0 mmol) were combined with DMF (100 mL) and DIEA (15.13 mL, 87.0 mmol). The reaction was stirred at room temperature overnight. The brown solution was concentrated, diluted with saturated NaHCO3, and extracted with EtOAc (2×). The combined organic layers were washed with brine, dried (MgSO4), filtered, and evaporated. The solid residue was triturated with CH2Cl2 and filtered to isolate the title compound as a colorless solid.