m-Chloroperbenzoic acid → HCID 11259470, compound

HRID 1951230Notes

Reaction equation

HRID 1951230 reaction equation
ClC1C=C(C=CC=1)C(OO)=[O:6].[CH2:12]([C:14]1[O:18][C:17]([CH2:19][CH2:20][NH:21][C:22]([NH:24][C:25]2[S:26][C:27]([C:31]3[CH:36]=[C:35]([CH3:37])[N:34]=[C:33]([S:38]([CH3:40])=[O:39])[N:32]=3)=[C:28]([CH3:30])[N:29]=2)=[O:23])=[N:16][CH:15]=1)[CH3:13]>ClCCl>[CH2:12]([C:14]1[O:18][C:17]([CH2:19][CH2:20][NH:21][C:22]([NH:24][C:25]2[S:26][C:27]([C:31]3[CH:36]=[C:35]([CH3:37])[N:34]=[C:33]([S:38]([CH3:40])(=[O:6])=[O:39])[N:32]=3)=[C:28]([CH3:30])[N:29]=2)=[O:23])=[N:16][CH:15]=1)[CH3:13]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acid2×HCID 11281950HCID 11281950, compound

Product 1

HCID 11259470HCID 11259470, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Meta-chloroperoxybenzoic acid or m-CPBA (57-86% purity, 0.438 g, 1.8 mmol) is added in portions to a rapidly stirring solution of 1-[2-(5-ethyl-oxazol-2-yl)-ethyl]-3-[5-(2-methane-sulfinyl-6-methyl-pyrimidin-4-yl)-4-methyl-thiazol-2-yl]-urea (0.31 g, 0.74 mmol) in dry dichloromethane (5 ml) at room temperature. After 2 hours the mixture is diluted with dichloromethane and washed with aqueous sodium thiosulfite and brine. The organic extract is separated, dried over MgSO4 and the solvent is removed. Purification by chromatography on silica, eluting with EtOAc, MeOH (97:3) affords the titled compound.

Workup

  1. washwashed with aqueous sodium thiosulfite and brine
  2. extractionThe organic extract
  3. customis separated
  4. dry with materialdried over MgSO4
  5. customthe solvent is removed
  6. customPurification by chromatography on silica
  7. washeluting with EtOAc, MeOH (97:3)

Sources & evidence

ORD record
ord-06eaeabf970a4c30a846f824fb38a3e8
Source dataset
uspto-grants-2013_03
Patent number
US08404684B2

Reaction notes

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