m-Chloroperbenzoic acid → HCID 178502003, compound

HRID 464784Notes

Reaction equation

HRID 464784 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([NH:8][C:9]([O:11][CH3:12])=[O:10])[CH:5]=[C:4]([O:13][S:14]([C:17]2[CH:22]=[CH:21][C:20]([CH3:23])=[CH:19][CH:18]=2)(=[O:16])=[O:15])[N:3]=1.ClC1C=CC=C(C(OO)=[O:32])C=1>C(Cl)Cl.CO>[NH2:1][C:2]1[N+:7]([O-:32])=[C:6]([NH:8][C:9]([O:11][CH3:12])=[O:10])[CH:5]=[C:4]([O:13][S:14]([C:17]2[CH:22]=[CH:21][C:20]([CH3:23])=[CH:19][CH:18]=2)(=[O:16])=[O:15])[N:3]=1

Participants

5

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 12857764Methyl 2-amino-6-[(p-tolylsulfonyl)oxy]-4-pyrimidinecarbamate

Product 1

HCID 178502003HCID 178502003, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

350 g of methyl 2-amino-6-[(p-tolylsulfonyl)oxy]-4-pyrimidinecarbamate are suspended in 6.3 l of methylene chloride and 1 l of methanol. At room temperature there are added thereto 370 g of m-chloroperbenzoic acid and the mixture is stirred for a further 16 hours. The yellowish solution is subsequently extracted with 3 l of 2N soda solution. The aqueous phase is extracted with 1 l of methylene chloride. The combined organic phases are washed with 2 l of water and evaporated in vacuo. The crystalline residue is suspended in 1.5 l of ether while stirring. The pale yellowish crystals are filtered off under suction and washed with 0.5 l of ether. After drying at 40° in vacuo, there is obtained methyl 2-amino-6-[(p-tolylsulfonyl)oxy]-4-pyrimidinecarbamate-3-oxide.

Workup

  1. additionAt room temperature there are added
  2. extractionThe yellowish solution is subsequently extracted with 3 l of 2N soda solution
  3. extractionThe aqueous phase is extracted with 1 l of methylene chloride
  4. washThe combined organic phases are washed with 2 l of water
  5. customevaporated in vacuo
  6. filtrationThe pale yellowish crystals are filtered off under suction
  7. washwashed with 0.5 l of ether
  8. customAfter drying at 40° in vacuo

Sources & evidence

ORD record
ord-04d4688b5ef24524bd2d281d4d537b31
Source dataset
uspto-grants-1985_10
Patent number
US04549019

Reaction notes

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