Methyl 4-aminothiophene-3-carboxylate → N-(5-bromopentyl)-N'-(4-carbomethoxythien-3-yl)urea

HRID 2165195Notes

Reaction equation

HRID 2165195 reaction equation
[NH2:1][C:2]1[C:3]([C:7]([O:9][CH3:10])=[O:8])=[CH:4][S:5][CH:6]=1.[Br:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][N:17]=[C:18]=[O:19]>C1(C)C=CC=CC=1>[Br:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][NH:17][C:18]([NH:1][C:2]1[C:3]([C:7]([O:9][CH3:10])=[O:8])=[CH:4][S:5][CH:6]=1)=[O:19]

Participants

4

Reactant 2

HCID 2777610Methyl 4-aminothiophene-3-carboxylateHCID 144828831-Bromo-5-isocyanatopentane

Product 1

HCID 15697668N-(5-bromopentyl)-N'-(4-carbomethoxythien-3-yl)ureaYield 98%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Methyl 4-aminothiophene-3-carboxylate was reacted with one equivalent of 5-bromopentylisocyanate in toluene at room temperature for 4 hours to produce N-(5-bromopentyl)-N'-(4-carbomethoxythien-3-yl]urea as a tan solid (98%). This material was recrystallized from CH2Cl2 /ether/hexane to afford the urea as a white solid, mp 92°-93.5° C.

Sources & evidence

ORD record
ord-00196413812543f780b9ae8faf4dd024
Source dataset
uspto-grants-1990_07
Patent number
US04939137

Reaction notes

Loading…