Methane → 6-[(Trifluoromethyl)sulfanyl]-1,3-benzothiazol-2-amine

HRID 2254641Notes

Reaction equation

HRID 2254641 reaction equation
[F:1][C:2]([F:12])([F:11])[S:3][C:4]1[CH:10]=[CH:9][C:7]([NH2:8])=[CH:6][CH:5]=1.[S-:13][C:14]#[N:15].[K+].BrBr.C>C(O)(=O)C>[F:12][C:2]([F:11])([F:1])[S:3][C:4]1[CH:10]=[CH:9][C:7]2[N:8]=[C:14]([NH2:15])[S:13][C:6]=2[CH:5]=1

Participants

6

Reactant 4

HCID 297MethaneHCID 24408BromineHCID 1230544-((Trifluoromethyl)thio)anilineHCID 516872Potassium thiocyanate

Product 1

HCID 27359646-[(Trifluoromethyl)sulfanyl]-1,3-benzothiazol-2-amineYield 58.1%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Conditions

Temperature
10 °C

Procedure

The procedure is as in Example 1, starting with 4-trifluoromethylthioaniline (3.85 g), potassium thiocyanate (7 g) and bromine (1 cc) in acetic acid (30 cc). The light brown crude product is taken up with acetic acid (250 cc) at 80° C. and the solution obtained is treated with decolorizing charcoal (0.4 g) and filtered; the filtrate is cooled to about 10° C., diluted with water (150 cc) and alkalinized with 28% strength ammonia solution (400 cc). The precipitate obtained is drained, dried in the air and recrystallized in a mixture of cyclohexane (250 cc) and isopropyl ether (30 cc). 6-Trifluoromethylthio-2-benzothiazolamine (2.9 g), m.p. 155° C., is obtained.

Workup

  1. customthe solution obtained
  2. filtrationfiltered
  3. additiondiluted with water (150 cc)
  4. customThe precipitate obtained
  5. customdried in the air
  6. customrecrystallized in a mixture of cyclohexane (250 cc) and isopropyl ether (30 cc)

Sources & evidence

ORD record
ord-8d6ef71918a342e29282f6d1ad274b93
Source dataset
uspto-grants-1993_08
Patent number
US05236940

Reaction notes

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