m-Chloroperbenzoic acid → HCID 178459829, compound

HRID 1091513Notes

Reaction equation

HRID 1091513 reaction equation
[F:1][C:2]([F:17])([F:16])[C:3]1[CH:8]=[CH:7][N:6]=[C:5]([NH:9][C:10](=[O:15])[O:11][C:12]([CH3:14])=[CH2:13])[CH:4]=1.C1C=C(Cl)C=C(C(OO)=[O:26])C=1>C(Cl)(Cl)Cl>[O-:26][N+:6]1[CH:7]=[CH:8][C:3]([C:2]([F:16])([F:1])[F:17])=[CH:4][C:5]=1[NH:9][C:10](=[O:15])[O:11][C:12]([CH3:14])=[CH2:13]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 59232120Isopropenyl [4-(trifluoromethyl)pyridin-2-yl]carbamate

Product 1

HCID 178459829HCID 178459829, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Isopropenyl [4-(trifluoromethyl)pyridin-2-yl]carbamate (1.2 g, 5.0 mmol) was suspended in CHCl3 (20 mL) and treated with m-CPBA (841 mg, 5.0 mmol). The reaction was stirred at rt overnight. The reaction was quenched with satd. NaHCO3 and extracted with CHCl3. The organic layer was dried (MgSO4) and concentrated. The crude residue was purified over silica using CH2Cl2 as the eluting solvent. An amber oil was collected (620 mg, 47%); 1H-NMR (DMSO-d6) δ 10.2 (s, 1H), 8.56 (d, J=6.9 Hz, 1H), 8.25 (d, J=2.6 Hz, 1H), 7.52 (ddd, dd, J1=6.8 Hz, J2=2.5 Hz, J3=0.6 Hz, 1H), 4.85 (q, J=1.2 Hz, 1H), 4.80 (d, J=1.2 Hz, 1H), 1.94 (d, J=0.4 Hz, 3H).

Workup

  1. customThe reaction was quenched with satd
  2. extractionNaHCO3 and extracted with CHCl3
  3. dry with materialThe organic layer was dried (MgSO4)
  4. concentrationconcentrated
  5. customThe crude residue was purified over silica
  6. customAn amber oil was collected (620 mg, 47%)

Sources & evidence

ORD record
ord-0ce8402c2ef5405e97e6e461ccda6622
Source dataset
uspto-grants-2012_03
Patent number
US08129379B2

Reaction notes

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