Acetic Acid → 2-Amino-5-bromobenzene-1-thiol
Reaction equation
[OH-].[K+].NC1[S:5][C:6]2[CH:12]=[C:11]([Br:13])[CH:10]=[CH:9][C:7]=2[N:8]=1.C(O)(=O)C>O>[NH2:8][C:7]1[CH:9]=[CH:10][C:11]([Br:13])=[CH:12][C:6]=1[SH:5]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
Potassium hydroxide (39.6 g) was dissolved at 0° C. in water (80 mL), and 2-amino-6-bromobenzothiazole (6.87 g) was added to the solution, followed by refluxing under heating overnight. The mixture was returned to room temperature, and then neutralized with 5N aqueous acetic acid solution. The precipitated crystals were recovered through filtration, washed with water, and dried under reduced pressure with heating, followed by recrystallization from isopropyl ether, to thereby yield the title compound (3.87 g).
Workup
- temperatureby refluxing
- temperatureunder heating overnight
- customwas returned to room temperature
- filtrationThe precipitated crystals were recovered through filtration
- washwashed with water
- customdried under reduced pressure
- temperaturewith heating
- customfollowed by recrystallization from isopropyl ether
Sources & evidence
- ORD record
- ord-95dfb255a5eb49f497aad75ae6f1451b
- Source dataset
- uspto-grants-2011_09
- Patent number
- US08022075B2
Reaction notes
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