Triethylamine → 2-Amino-4-trifluoromethoxybenzothiazol

HRID 1063074Notes

Reaction equation

HRID 1063074 reaction equation
Br[C:2]1[CH:11]=[C:10]([O:12][C:13]([F:16])([F:15])[F:14])[C:5]2[N:6]=[C:7]([NH2:9])[S:8][C:4]=2[CH:3]=1.C(N(CC)CC)C>[Pd].C(O)C>[F:16][C:13]([F:14])([F:15])[O:12][C:10]1[C:5]2[N:6]=[C:7]([NH2:9])[S:8][C:4]=2[CH:3]=[CH:2][CH:11]=1

Participants

5

Reactant 2

HCID 8471TriethylamineHCID 22283228HCID 22283228, compound

Product 1

HCID 106334172-Amino-4-trifluoromethoxybenzothiazolYield 73%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

6-Bromo-4-trifluoromethoxy-benzothiazol-2-ylamine (157 mg, 0.50 mg), triethylamine (0.21 ml, 1.5 mmol) and palladium on carbon (10%, 15 mg) are suspended in ethanol (12 ml) and hydrogenated at atmospheric pressure for 96 h. The catalyst was filtered off and the solution evaporated to dryness. The residue was dissolved in ethyl acetate, washed three times with water, dried and the solvent removed in vacuo. The product is obtained as brown solid (85 mg, 73%). MS: m/e=235 (M+H+).

Workup

  1. filtrationThe catalyst was filtered off
  2. customthe solution evaporated to dryness
  3. dissolutionThe residue was dissolved in ethyl acetate
  4. washwashed three times with water
  5. customdried
  6. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-f13d7e6f93ff478d821a07edb75d9872
Source dataset
uspto-grants-2005_11
Patent number
US06963000B2

Reaction notes

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