Phenyl chloroformate → Diphenyl (5-bromo-1,3-thiazol-2-yl)imidodicarbonate
Reaction equation
Cl[C:2]([O:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:3].Br.[Br:12][C:13]1[S:17][C:16]([NH2:18])=[N:15][CH:14]=1>N1C=CC=CC=1>[Br:12][C:13]1[S:17][C:16]([N:18]([C:2]([O:4][C:5]2[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=2)=[O:3])[C:2]([O:4][C:5]2[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=2)=[O:3])=[N:15][CH:14]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
Phenyl chloroformate (1.4 ml, 11.0 mmol) was slowly added to a suspension of 5-bromo-thiazol-2-ylamine hydrobromide (1.3 g, 5.0 mmol) in 20 ml pyridine under an argon atmosphere. The reaction mixture was stirred for 3 h at room temperature and then concentrated under reduced pressure. The residue was suspended in water and acidified using conc. HCl to yield light brown crystals (2.3 g, 93%), m/e 419.2 (MH+).