3-(2-bromoethyl)thiophene → HCID 21520086, compound
Reaction equation
[NH2:1][C:2]1[C:3]([O:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[C:4]([SH:11])[CH:5]=[C:6]([CH:10]=1)[C:7]([OH:9])=[O:8].BrC[CH2:21][C:22]1[CH:26]=[CH:25][S:24][CH:23]=1>[OH-].[Na+]>[NH2:1][C:2]1[C:3]([O:12][C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=2)=[C:4]([S:11][CH2:21][C:22]2[CH:26]=[CH:25][S:24][CH:23]=2)[CH:5]=[C:6]([CH:10]=1)[C:7]([OH:9])=[O:8]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of 5-amino-3-mercapto-4-phenoxybenzoic acid (2.5 g) in 0.5 N sodium hydroxide (100 ml), a solution of 3-bromoethylthiophene (3.5 g in benzene (20 ml)) is added. The reaction mixture is stirred for 2 hours at room temperature. After extraction with additional benzene, the aqueous layer is acidified by addition of 4 N hydrochloric acid to precipitate 5-amino-4-phenoxy-3-(3-thienylmethylthio)benzoic acid. After collection by filtration, recrystallisation from aqueous ethanol and drying, the compound is obtained with a melting point of 153°-155° C.