Potassium Carbonate → Ethyl 5-ethyl-2-(2-nitroanilino)-thiophene-3-carboxylate

HRID 427024Notes

Reaction equation

F[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N+:8]([O-:10])=[O:9].[NH2:11][C:12]1[S:13][C:14]([CH2:22][CH3:23])=[CH:15][C:16]=1[C:17]([O:19][CH2:20][CH3:21])=[O:18].C(=O)([O-])[O-].[K+].[K+]>CS(C)=O>[CH2:22]([C:14]1[S:13][C:12]([NH:11][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=2[N+:8]([O-:10])=[O:9])=[C:16]([C:17]([O:19][CH2:20][CH3:21])=[O:18])[CH:15]=1)[CH3:23]

Participants

Conditions

Temperature: 100 °C

Procedure

o-Fluoronitrobenzene (b 56.4 g, 0.4 mol) and ethyl 2-amino-5-ethylthiophene-3-carboxylate (100 g, 0.5 mol) were dissolved in dry dimethylsulphoxide (320 ml). The stirred solution, under nitrogen, was heated in an oil bath. When the internal temperature reached 60° C., potassium carbonate (55 g, 0.4 mol) was added and the mixture stirred at 100° C. until GLC indicated that all the o-fluoronitrobenzene had been consumed (6.5 hours). The mixture was then poured onto ice-water, acidified with concentrated hydrochloric acid and extracted with methylene chloride. The combined extracts were washed with water, dried (MgSO4) and the solvent evaporated to give a red semi-solid which was recrystallised from ethanol to give the title product as a solid (m.p. 66°-68° C.).

Workup

temperatureThe stirred solution, under nitrogen, was heated in an oil bath
customreached 60° C.
customhad been consumed (6.5 hours)
additionThe mixture was then poured onto ice-water
extractionextracted with methylene chloride
washThe combined extracts were washed with water
dry with materialdried (MgSO4)
customthe solvent evaporated
customto give a red semi-solid which
customwas recrystallised from ethanol

Sources & evidence

ORD record: ord-24a0ebf52c4b446781ca2e07a5a57159
Source dataset: uspto-grants-1979_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04172831

Reaction notes

Loading…