Water → HCID 21243220, compound

HRID 1905874Notes

Reaction equation

HRID 1905874 reaction equation
COC1C=CC([C:9]2[N:14]([CH3:15])[C:13](=[O:16])[N:12]([CH3:17])[C:11](=[N:18][C:19]3[C:24]([CH3:25])=[CH:23][C:22]([CH3:26])=[CH:21][C:20]=3[CH3:27])[CH:10]=2)=CC=1SC.ClC1C=CC=C(C(OO)=O)C=1.O>CN(C)C=O>[CH3:15][N:14]1[CH:9]=[CH:10][C:11](=[N:18][C:19]2[C:20]([CH3:27])=[CH:21][C:22]([CH3:26])=[CH:23][C:24]=2[CH3:25])[N:12]([CH3:17])[C:13]1=[O:16]

Participants

5

Reactant 3

HCID 962WaterHCID 70297m-Chloroperbenzoic acidHCID 13608182HCID 13608182, compound

Product 1

HCID 21243220HCID 21243220, compoundYield 82.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 3,4-dihydro-6-(4-methoxy-3-methylthiophenyl)-1,3-dimethyl-4-(2,4,6-trimethylphenylimino)-2(1H)-pyrimidinone (1.5 g) in N,N-dimethylformamide (15 ml) was added m-chloroperbenzoic acid (1.58 g), and stirred at 5°-10° C. for 30 minutes, and at ambient temperature for 5 hours. To the reaction mixture was added water (50 ml), and extracted with ethyl acetate. The organic layer was washed with aqueous sodium bicarbonate solution, dried over sodium sulfate, and evaporated. The residue was chromatographed on silica gel, eluting with chloroform. The fractions containing a sulfonyl compound were collected, dissolved in 1-N-hydrochloric acid and neutralized by aqueous sodium bicarbonate solution to give powdery 3,4-dihydro-6-(4- ro methoxy-3-methylsulfonylphenyl)-1,3-dimethyl-4-(2,4,6-trimethylphenylimino)-2(1H)-pyrimidinone (0.78 g).

Workup

  1. waitat ambient temperature for 5 hours
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with aqueous sodium bicarbonate solution
  4. dry with materialdried over sodium sulfate
  5. customevaporated
  6. customThe residue was chromatographed on silica gel
  7. washeluting with chloroform
  8. additionThe fractions containing a sulfonyl compound
  9. customwere collected
  10. dissolutiondissolved in 1-N-hydrochloric acid

Sources & evidence

ORD record
ord-098f371fab434de4b0439d61c52c1830
Source dataset
uspto-grants-1987_03
Patent number
US04649142

Reaction notes

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