Potassium Carbonate → HCID 59594504, compound

HRID 1428923Notes

Reaction equation

HRID 1428923 reaction equation
FC(F)(F)[C:3]([N:5](C)[C:6]1[CH:15]=[CH:14][C:9]2[N:10]=[C:11]([CH3:13])[O:12][C:8]=2[CH:7]=1)=O.C([O-])([O-])=O.[K+].[K+]>CO.O>[CH3:3][NH:5][C:6]1[CH:15]=[CH:14][C:9]2[N:10]=[C:11]([CH3:13])[O:12][C:8]=2[CH:7]=1

Participants

5

Reactant 2

HCID 11430Potassium CarbonateHCID 90418757HCID 90418757, compound

Product 1

HCID 59594504HCID 59594504, compoundYield 81.2%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a solution of crude 2,2,2-trifluoro-N-methyl-N-(2-methylbenzo[d]oxazol-6-yl)acetamide (16.5 g, 63.0 mmol) in MeOH (440 mL) and water (73 mL) was added K2CO3 (35.3 g, 25.5 mmol). The reaction mixture was stirred at reflux for 3 h, then concentrated under vacuum, diluted with water (50 mL), extracted with EtOAc (2×50 mL). The organics were washed with brine, dried over Na2SO4, and concentrated to obtain crude N,2-dimethylbenzo[d]oxazol-6-amine (8.3 g), (MS: ESI +ve, 163.12 [M+H]); 1H NMR: (400 MHz, DMSO) δ: 2.51 (s, 3H), 2.56 (s, 3H), 5.87-5.85 (m, 1H), 6.57-6.53 (m, 1H), 6.65-6.64 (d, J=2.4, 1H), 7.31-7.28 (t, 1H).

Workup

  1. temperatureat reflux for 3 h
  2. concentrationconcentrated under vacuum
  3. additiondiluted with water (50 mL)
  4. extractionextracted with EtOAc (2×50 mL)
  5. washThe organics were washed with brine
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-bab57fa6bfde49bebd4844b8b9f38e21
Source dataset
uspto-grants-2015_01
Patent number
US08937178B2

Reaction notes

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