m-Chloroperbenzoic acid → HCID 178459829, compound

HRID 1099311Notes

Reaction equation

HRID 1099311 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, 1 H), 8.56 (d, J=6.9 Hz, 1 H), 8.25 (d, J=2.6 Hz, 1 H), 7.52 (ddd, dd, J1=6.8 Hz, J2=2.5 Hz, J3=0.6 Hz, 1 H), 4.85 (q, J=1.2 Hz, 1 H), 4.80 (d, J=1.2 Hz, 1 H), 1.94 (d, J=0.4 Hz, 3 H).

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-168026679c6b4952ab7ea6b4a1a35feb
Source dataset
uspto-grants-2012_03
Patent number
US08143393B2

Reaction notes

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