Triethylamine → 2-Amino-4-trifluoromethoxybenzothiazol

HRID 2308551Notes

Reaction equation

HRID 2308551 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-76e67a47bafd4902afa22d904ff1256a
Source dataset
uspto-grants-2004_12
Patent number
US06835732B2

Reaction notes

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