m-Chloroperbenzoic acid → HCID 19860379, compound

HRID 1721876Notes

Reaction equation

HRID 1721876 reaction equation
[CH3:1][CH:2]([NH:4][C:5]([NH:7][S:8]([C:11]1[C:12]([NH:19][C:20]2[CH:25]=[CH:24][CH:23]=[C:22]([CH3:26])[CH:21]=2)=[N:13][C:14]([S:17][CH3:18])=[N:15][CH:16]=1)(=[O:10])=[O:9])=[O:6])[CH3:3].ClC1C=C(C=CC=1)C(OO)=[O:32]>C(Cl)Cl>[CH3:3][CH:2]([NH:4][C:5]([NH:7][S:8]([C:11]1[C:12]([NH:19][C:20]2[CH:25]=[CH:24][CH:23]=[C:22]([CH3:26])[CH:21]=2)=[N:13][C:14]([S:17]([CH3:18])=[O:32])=[N:15][CH:16]=1)(=[O:10])=[O:9])=[O:6])[CH3:1]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 19860397HCID 19860397, compound

Product 1

HCID 19860379HCID 19860379, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

N-[[(1-Methylethyl)amino]carbonyl]-4-[(3-methylphenyl)amino]-2-(methylthio)-5-pyrimidinesulfonamide (4.46 g, 11.29 mmol) was suspended in methylene chloride (250 mL) and m-chloroperoxybenzoic acid (2.44 g, 11.29 mml) was added as a solid. The mixture was then stirred until it became homogeneous. The methylene chloride was removed under reduced pressure and the residue was triturated with hot tert-butyl methyl ether (100 mL). The beige solid was filtered, washed with tert-butyl methyl ether and dried in a vacuum oven at 65° C. for three hours to yield 3.75 g (9.12 mmol, 81%) of pure product as a white solid.

Workup

  1. customThe methylene chloride was removed under reduced pressure
  2. customthe residue was triturated with hot tert-butyl methyl ether (100 mL)
  3. filtrationThe beige solid was filtered
  4. washwashed with tert-butyl methyl ether
  5. customdried in a vacuum oven at 65° C. for three hours

Sources & evidence

ORD record
ord-007963f5941d4bb489b1d4b7ab35fbac
Source dataset
uspto-grants-1989_08
Patent number
US04853389

Reaction notes

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