Bromine → Benzo(d)thiazol-2-amine

HRID 2254645Notes

Reaction equation

HRID 2254645 reaction equation
FC(F)(O[C:7]1[CH:13]=[CH:12][C:10]([NH2:11])=[CH:9][CH:8]=1)C(F)F.[S-:15][C:16]#[N:17].[K+].BrBr>C(O)(=O)C>[S:15]1[C:9]2[CH:8]=[CH:7][CH:13]=[CH:12][C:10]=2[N:11]=[C:16]1[NH2:17]

Participants

5

Reactant 3

HCID 24408BromineHCID 516872Potassium thiocyanateHCID 27766304-(1,1,2,2-tetrafluoroethoxy)aniline

Product 1

HCID 8706Benzo(d)thiazol-2-amineYield 27.8%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

The procedure is as in Example 1, starting with 4-(1,1,2,2-tetrafluoroethoxy)aniline (10 g), potassium thiocyanate 18.5 g), bromine (2.4 cc) and acetic acid (80 cc). After purification on a column of silica (1 kg; particle size: 0.063-0.200 mm), eluting with a mixture of cyclohexane and ethyl acetate (50:50 by volume), and recrystallization in toluene (22 cc), 6- 1,1,2,2-tetrafluoroethoxy)-2-benzothiazolamine (2 g), m.p. 161° C., is obtained.

Workup

  1. customAfter purification on a column of silica (1 kg; particle size: 0.063-0.200 mm)
  2. washeluting with a mixture of cyclohexane and ethyl acetate (50:50 by volume), and recrystallization in toluene (22 cc)

Sources & evidence

ORD record
ord-25b06cfefa024a70ba464cf0d57b6020
Source dataset
uspto-grants-1993_08
Patent number
US05236940

Reaction notes

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