m-Chloroperbenzoic acid → HCID 13260598, compound

HRID 463074Notes

Reaction equation

HRID 463074 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[S:7][CH2:8][CH2:9][CH2:10][CH2:11][O:12][C:13]1[CH:14]=[CH:15][C:16]2[NH:21][C:20](=[O:22])[O:19][C:18]([CH3:24])([CH3:23])[C:17]=2[CH:25]=1.ClC1C=CC=C(C(OO)=[O:34])C=1>C(Cl)(Cl)Cl>[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[S:7]([CH2:8][CH2:9][CH2:10][CH2:11][O:12][C:13]1[CH:14]=[CH:15][C:16]2[NH:21][C:20](=[O:22])[O:19][C:18]([CH3:23])([CH3:24])[C:17]=2[CH:25]=1)=[O:34]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acid2×HCID 13260525HCID 13260525, compound

Product 1

HCID 13260598HCID 13260598, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A quantity of 3.58 gm (0.01 mol) 6-[4-(2-pyridylmercapto)-butoxy]-4,4-dimethyl-4H-3,1-benzoxazin-2-one is dissolved in 100 ml of chloroform and mixed with 4.3 gm (0.025 mol) of m-chloroperbenzoic acid, under stirring. After stirring for two hours, a further 2 gm of m-chloroperbenzoic acid are added, and the mixture is left to stand overnight. The chloroform phase is extracted with water, the organic phase is dried with sodium sulfate, and the chloroform is distilled off. The non-uniform residue is purified by column chromatography [silica gel, particle size of 0.05 to 0.2 mm; chloroform/ethanol (40:1)]. The uniform fractions are combined, and the residue is triturated with ethyl acetate/ether. The crystals thus obtained are subjected to suction filtration and dried at 50° C.

Workup

  1. stirringAfter stirring for two hours
  2. waitthe mixture is left
  3. extractionThe chloroform phase is extracted with water
  4. dry with materialthe organic phase is dried with sodium sulfate
  5. distillationthe chloroform is distilled off
  6. customThe non-uniform residue is purified by column chromatography [silica gel, particle size of 0.05 to 0.2 mm; chloroform/ethanol (40:1)]
  7. customthe residue is triturated with ethyl acetate/ether
  8. customThe crystals thus obtained
  9. filtrationare subjected to suction filtration
  10. customdried at 50° C.

Sources & evidence

ORD record
ord-f2fb0ff000e245ac9092804342f80ae8
Source dataset
uspto-grants-1985_05
Patent number
US04518597

Reaction notes

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