Bromine → 4-Methyl-6-trifluoromethoxy-2-benzothiazolamine

HRID 2254642Notes

Reaction equation

HRID 2254642 reaction equation
[F:1][C:2]([F:13])([F:12])[O:3][C:4]1[CH:10]=[CH:9][C:7]([NH2:8])=[C:6]([CH3:11])[CH:5]=1.[S-:14][C:15]#[N:16].[K+].BrBr>C(O)(=O)C.C1CCCCC1>[CH3:11][C:6]1[C:7]2[N:8]=[C:15]([NH2:16])[S:14][C:9]=2[CH:10]=[C:4]([O:3][C:2]([F:12])([F:13])[F:1])[CH:5]=1

Participants

6

Reactant 3

HCID 24408BromineHCID 516872Potassium thiocyanateHCID 27755462-Methyl-4-(trifluoromethoxy)aniline

Product 1

HCID 146744814-Methyl-6-trifluoromethoxy-2-benzothiazolamineYield 71.1%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 8078CyclohexaneSolvent

Procedure

The procedure is as in Example 1, starting with 4-trifluoromethoxy-2-methylaniline (0.65 g), potassium thiocyanate (1.3 g) and bromine (0.35 cc) in acetic acid (12 cc). After purification on a column of silica (200 g; particle size: 0.063-0.200 mm), eluting with a cyclohexane/ethyl acetate mixture (50:50 by volume), the white solid obtained (0.65 g) is ground in cyclohexane (20 cc), drained and dried at 60° C. under reduced pressure (1 mm Hg; 0.13 kPa), to give 4-methyl-6-trifluoromethoxy-2-benzothiazolamine (0.6 g), m.p. 162° C.

Workup

  1. customAfter purification on a column of silica (200 g; particle size: 0.063-0.200 mm)
  2. washeluting with a cyclohexane/ethyl acetate mixture (50:50 by volume)
  3. customthe white solid obtained (0.65 g)
  4. customdried at 60° C. under reduced pressure (1 mm Hg; 0.13 kPa)

Sources & evidence

ORD record
ord-cc58156e459b4f3b876305daae925f44
Source dataset
uspto-grants-1993_08
Patent number
US05236940

Reaction notes

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