Methanol → HCID 178502002, compound

HRID 464778Notes

Reaction equation

HRID 464778 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.CN1CCOCC1.Cl[C:33]([O:35][CH3:36])=[O:34].CO>C(Cl)Cl.O1CCCC1.O>[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:33]([O:35][CH3:36])=[O:34])[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

8

Reactant 4

HCID 887MethanolHCID 6586Methyl chloroformateHCID 79724-MethylmorpholineHCID 178502003HCID 178502003, compound

Product 1

HCID 178502002HCID 178502002, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

3.5 g of crude methyl 2-amino-6-[(p-tolylsulfonyl)oxy]-4-pyrimidinecarbamate-3-oxide are dissolved in 100 ml of methylene chloride and 50 ml of tetrahydrofuran. At 0° there are added thereto 2.2 g of N-methylmorpholine and subsequently 1.45 ml of methyl chloroformate in 20 ml of methylene chloride. The mixture is stirred at 0° for 1 hour and then at room temperature for 2 hours and thereupon treated with a small amount of methanol and water. The organic phase is separated, dried and evaporated. The residue is recrystallized from methylene chloride and ether, there being obtained pure dimethyl 6-[(p-tolylsulfonyl)oxy]-2,4-pyrimidinedicarbamate-3-oxide of melting point 178°-179°.

Workup

  1. additionAt 0° there are added
  2. waitat room temperature for 2 hours
  3. customThe organic phase is separated
  4. customdried
  5. customevaporated
  6. customThe residue is recrystallized from methylene chloride and ether, there

Sources & evidence

ORD record
ord-149eb55cdee540ceb1a328498b1e4da1
Source dataset
uspto-grants-1985_10
Patent number
US04549019

Reaction notes

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