Hydrogen Peroxide → [6-Acetamido-2-imino-4-(4-methylphenyl)sulfonyloxypyrimidin-1-yl] acetate

HRID 868638Notes

Reaction equation

HRID 868638 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([O:8][S:9]([C:12]2[CH:18]=[CH:17][C:15]([CH3:16])=[CH:14][CH:13]=2)(=[O:11])=[O:10])[CH:5]=[C:4]([NH2:19])[N:3]=1.OO.[C:22]([O:25]C(=O)C)(=[O:24])[CH3:23].[O:29]1CC[CH2:31][CH2:30]1>>[C:30]([NH:19][C:4]1[N:3]([O:25][C:22](=[O:24])[CH3:23])[C:2](=[NH:1])[N:7]=[C:6]([O:8][S:9]([C:12]2[CH:18]=[CH:17][C:15]([CH3:16])=[CH:14][CH:13]=2)(=[O:11])=[O:10])[CH:5]=1)(=[O:29])[CH3:31]

Participants

5

Reactant 4

HCID 784Hydrogen PeroxideHCID 7918Acetic AnhydrideHCID 8028TetrahydrofuranHCID 12661239HCID 12661239, compound

Product 1

HCID 140351385[6-Acetamido-2-imino-4-(4-methylphenyl)sulfonyloxypyrimidin-1-yl] acetateYield 68%

Procedure

84 g (0.3 mole) of 2,6-diamino-4-tosyloxypyrmidine are added to 1200 ml of anhydrous tetrahydrofuran. 40 ml of a 70% aqueous hydrogen peroxide solution are dropped to the obtained suspension at room temperature while stirring, whereupon the material is dissolved. While stirring 200 ml of acetic anhydride are added to the solution at 40° C. in an hour. After adding the mixture is stirred at 60° C. for further two hours. Then the solvent is evaporated in vacuo and the residue is allowed to stand in a refrigerator for a night. The separated material is filtered, washed with tetrahydrofuran and dried. In this way 77 g (68%) of the aimed compound are obtained.

Workup

  1. dissolutionis dissolved
  2. additionare added to the solution at 40° C. in an hour
  3. additionAfter adding the mixture
  4. stirringis stirred at 60° C. for further two hours
  5. customThen the solvent is evaporated in vacuo
  6. waitto stand in a refrigerator for a night
  7. filtrationThe separated material is filtered
  8. washwashed with tetrahydrofuran
  9. customdried

Sources & evidence

ORD record
ord-10530ecdb02447b1a0539fe3ff9413e8
Source dataset
uspto-grants-1988_10
Patent number
US04780537

Reaction notes

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