Hexane → HCID 178502003, compound

HRID 464770Notes

Reaction equation

HRID 464770 reaction equation
ClC1C=CC=C(C(OO)=[O:9])C=1.[NH2:12][C:13]1[N:18]=[C:17]([NH:19][C:20]([O:22][CH3:23])=[O:21])[CH:16]=[C:15]([O:24][S:25]([C:28]2[CH:33]=[CH:32][C:31]([CH3:34])=[CH:30][CH:29]=2)(=[O:27])=[O:26])[N:14]=1.CCCCCC>C(Cl)Cl.CO>[NH2:12][C:13]1[N+:18]([O-:9])=[C:17]([NH:19][C:20]([O:22][CH3:23])=[O:21])[CH:16]=[C:15]([O:24][S:25]([C:28]2[CH:33]=[CH:32][C:31]([CH3:34])=[CH:30][CH:29]=2)(=[O:27])=[O:26])[N:14]=1

Participants

6

Reactant 3

HCID 8058HexaneHCID 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

61.1 g (0.314 mol) of 88% m-chloroperbenzoic acid are added to a suspension of 50.7 g (0.15 mol) of methyl 2-amino-6-[(p-toluenesulfonyl)oxy]-4-pyrimidinecarbamate in 1800 ml of methylene chloride and 300 ml of methanol. The solution, which becomes clear after 2 hours, is stirred at room temperature overnight and thereafter warmed to 40° for 8 hours. 1800 ml of hexane are added to this solution and the mixture is cooled to 0° overnight, whereby there forms a crystalline precipitate which is filtered off under suction and dried. The mother liquor is concentrated to approximately 400 ml under reduced pressure, there being obtained a further crystalline precipitate of methyl 2-amino-6-[(p-toluenesulfonyl)oxy]-4-pyrimidinecarbamate-3-oxide of melting point 144°-145°.

Workup

  1. temperaturewarmed to 40° for 8 hours
  2. temperaturethe mixture is cooled to 0° overnight
  3. filtrationis filtered off under suction
  4. customdried
  5. concentrationThe mother liquor is concentrated to approximately 400 ml under reduced pressure, there

Sources & evidence

ORD record
ord-dfca246f39804539b18f491087ed28e3
Source dataset
uspto-grants-1985_10
Patent number
US04549019

Reaction notes

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