m-Chloroperbenzoic acid → HCID 86753549, compound

HRID 342480Notes

Reaction equation

HRID 342480 reaction equation
ClC1C=CC=C(C(OO)=[O:9])C=1.[Cl:12][C:13]1[C:14]([NH:21][CH:22]2[CH2:27][CH2:26][C:25](=[CH:28][CH2:29][CH2:30][CH2:31][CH2:32][CH3:33])[CH2:24][CH2:23]2)=[N:15][CH:16]=[N:17][C:18]=1[CH2:19][CH3:20]>ClCCl>[Cl:12][C:13]1[C:14]([NH:21][CH:22]2[CH2:27][CH2:26][C:25]3([O:9][CH:28]3[CH2:29][CH2:30][CH2:31][CH2:32][CH3:33])[CH2:24][CH2:23]2)=[N:15][CH:16]=[N:17][C:18]=1[CH2:19][CH3:20]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 54076189HCID 54076189, compound

Product 1

HCID 86753549HCID 86753549, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 4.0 g (0.02 mol) of m-chloroperbenzoic acid (85% strength) in 25 ml of dichloromethane was slowly added dropwise at 0° C. to a solution of 6.4 g (0.02 mol) of 5-chloro-6-ethyl-4-(4-hexylidenecyclohexylamino)pyrimidine (WO 95 07894) in 25 ml of dichloromethane. Stirring of the mixture was continued at room temperature for 4 hours. After the mixture had been allowed to stand overnight, it was extracted by stirring with aqueous sodium hydrogen carbonate solution, and the organic phase was dried and concentrated. The crude product was chromatographed on silica gel (petroleum ether/ethyl acetate 4:1). First, 1.8 g (265.6% of theory) of the isomer having the higher Rf value (0.62) were eluted (colorless crystals, m.p.: 41°-42° C.), followed by 1.2 g (18.2% of theory) of isomer mixture and 0.22 g (3.3% of theory) of the isomer having the lower Rf value (0.53) as a colorless oil.

Workup

  1. waitto stand overnight
  2. extractionit was extracted
  3. stirringby stirring with aqueous sodium hydrogen carbonate solution
  4. customthe organic phase was dried
  5. concentrationconcentrated
  6. customThe crude product was chromatographed on silica gel (petroleum ether/ethyl acetate 4:1)
  7. washwere eluted (colorless crystals, m.p.: 41°-42° C.)

Sources & evidence

ORD record
ord-624a25e613ef4457802267440ea0cd26
Source dataset
uspto-grants-1999_01
Patent number
US05859009

Reaction notes

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