Hydrogen Peroxide → HCID 178501976, compound

HRID 1285193Notes

Reaction equation

HRID 1285193 reaction equation
OO.C1(=O)OC(=[O:7])C=C1.[Cl:10][C:11]1[N:16]=[C:15]([NH:17][C:18]([O:20][CH3:21])=[O:19])[N:14]=[C:13]([NH:22][C:23]([O:25][CH3:26])=[O:24])[CH:12]=1>C(Cl)Cl.C1C=CC=CC=1>[Cl:10][C:11]1[N:16]=[C:15]([NH:17][C:18]([O:20][CH3:21])=[O:19])[N+:14]([O-:7])=[C:13]([NH:22][C:23]([O:25][CH3:26])=[O:24])[CH:12]=1

Participants

6

Reactant 3

HCID 784Hydrogen PeroxideHCID 7923Maleic AnhydrideHCID 13424620HCID 13424620, compound

Product 1

HCID 178501976HCID 178501976, compound

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 6344DichloromethaneSolvent2×

Procedure

A mixture of 18.7 g (0.385 mol) of 70 percent hydrogen peroxide and 400 ml of methylene chloride, stirred under argon and cooled to about 0°, is treated with 49.0 g (0.5 mol) of maleic acid anhydride. The mixture is stirred at 0° for 5 minutes and subsequently treated dropwise over a period of 15 minutes with a solution of 13.0 g (0.05 mol) of dimethyl 6-chloro-2,4-pyrimidinedicarbamate in 1500 ml of methylene chloride in such a manner that the temperature does not exceed 2°. The cooling bath is removed, the mixture is stirred for a further 15.5 hours, cooled to 3° and filtered. The white solid residue is subsequently washed with 400 ml of semi-saturated ice-cold sodium carbonate solution and then with 100 ml of ice-water. The material obtained is taken up in 150 ml of benzene and evaporated. This procedure is repeated once more and then the residue is dried at 60° under vacuum. There is obtained dimethyl 6-chloro-2,4-pyrimidinedicarbamate 3-oxide as a white solid of melting point 224°-225°.

Workup

  1. temperaturecooled to about 0°
  2. stirringThe mixture is stirred at 0° for 5 minutes
  3. customdoes not exceed 2°
  4. customThe cooling bath is removed
  5. stirringthe mixture is stirred for a further 15.5 hours
  6. temperaturecooled to 3°
  7. filtrationfiltered
  8. washThe white solid residue is subsequently washed with 400 ml of semi-saturated ice-cold sodium carbonate solution
  9. customThe material obtained
  10. customevaporated
  11. customthe residue is dried at 60° under vacuum

Sources & evidence

ORD record
ord-fffb18ee128a429890b71c86f1f65fa5
Source dataset
uspto-grants-1986_01
Patent number
US04565869

Reaction notes

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