Water → HCID 178502002, compound

HRID 464785Notes

Reaction equation

HRID 464785 reaction equation
[NH2:1][C:2]1[N+:7]([O-:8])=[C:6]([NH:9][C:10]([O:12][CH3:13])=[O:11])[CH:5]=[C:4]([O:14][S:15]([C:18]2[CH:23]=[CH:22][C:21]([CH3:24])=[CH:20][CH:19]=2)(=[O:17])=[O:16])[N:3]=1.O.Cl[C:27]([O:29][CH3:30])=[O:28].C(=O)(O)[O-].[Na+]>C(Cl)Cl>[C:21]1([CH3:24])[CH:22]=[CH:23][C:18]([S:15]([O:14][C:4]2[N:3]=[C:2]([NH:1][C:27]([O:29][CH3:30])=[O:28])[N+:7]([O-:8])=[C:6]([NH:9][C:10]([O:12][CH3:13])=[O:11])[CH:5]=2)(=[O:17])=[O:16])=[CH:19][CH:20]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6586Methyl chloroformateHCID 516892Sodium BicarbonateHCID 178502003HCID 178502003, compound

Product 1

HCID 178502002HCID 178502002, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

150 g of methyl 2-amino-6-[(p-tolylsulfonyl)oxy]-4-pyrimidinecarbamate-3-oxide are suspended in 2 l of methylene chloride and 2 l of water while stirring. After cooling to 0°-5°, 50 ml of methyl chloroformate are added thereto. After stirring vigorously for about 10 minutes, the mixture is adjusted to a pH of 7-7.5 with about 150 g of sodium bicarbonate. The mixture is subsequently stirred at 0°-5° for a further 3 hours. The organic phase is separated and the aqueous phase is extracted with 1 l of methylene chloride. The combined organic phases are washed twice with 1 l of water each time, dried over sodium sulphate and evaporated in vacuo. There is obtained crude dimethyl 6-[(p-tolylsulfonyl)oxy]-2,4-pyrimidinedicarbamate-3-oxide which is used in the next step (a pure product of melting point 178°-180° can be obtained by digestion with ethyl acetate).

Workup

  1. temperatureAfter cooling to 0°-5°
  2. stirringThe mixture is subsequently stirred at 0°-5° for a further 3 hours
  3. customThe organic phase is separated
  4. extractionthe aqueous phase is extracted with 1 l of methylene chloride
  5. washThe combined organic phases are washed twice with 1 l of water each time
  6. dry with materialdried over sodium sulphate
  7. customevaporated in vacuo

Sources & evidence

ORD record
ord-934934e0a8124027b775ea22c6013d55
Source dataset
uspto-grants-1985_10
Patent number
US04549019

Reaction notes

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