Acetic Acid → 2-Amino-5-bromobenzene-1-thiol

HRID 910229Notes

Reaction equation

HRID 910229 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

HCID 176Acetic AcidHCID 14797Potassium HydroxideHCID 851492-Benzothiazolamine, 6-bromo-

Product 1

HCID 12090452-Amino-5-bromobenzene-1-thiolYield 63.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

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

  1. temperatureby refluxing
  2. temperatureunder heating overnight
  3. customwas returned to room temperature
  4. filtrationThe precipitated crystals were recovered through filtration
  5. washwashed with water
  6. customdried under reduced pressure
  7. temperaturewith heating
  8. 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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