Acetic Anhydride → AC1NR783

HRID 2172863Notes

Reaction equation

HRID 2172863 reaction equation
CC(OC(C)=O)=O.[CH3:8][S:9][C:10]1[NH:15][C:14](=[O:16])[CH:13]=[CH:12][N:11]=1.C1C(=O)N([Cl:24])C(=O)C1>CC(O)=O>[Cl:24][C:13]1[C:14](=[O:16])[NH:15][C:10]([S:9][CH3:8])=[N:11][CH:12]=1

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 31398ChlorosuccinimideHCID 798232-(Methylthio)-1H-pyrimidin-4-one

Product 1

HCID 5235666AC1NR783Yield 48.5%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
80 °C

Procedure

To a mixture of HOAc (500 mL) and Ac2O (10 mL) was added compound 2-(methylthio)pyrimidin-4(3H)-one (40 g, 0.28 mol). The resulting mixture was heated at 80° C. for 30 min to remove any moisture. Then NCS (49 g, 0.37 mol) was added at 50˜60° C. The resulting mixture was stirred at 50˜60° C. for 24 h. The mixture was then cooled to room temperature and was poured into ice-water (500 mL). The solid formed was collected and was treated with MeOH (100 mL) at reflux. Then the solid was filtered and dried on vacuum to give title compound (24 g, 48%) as a white solid.

Workup

  1. customto remove any moisture
  2. temperatureThe mixture was then cooled to room temperature
  3. customThe solid formed
  4. customwas collected
  5. additionwas treated with MeOH (100 mL)
  6. temperatureat reflux
  7. filtrationThen the solid was filtered
  8. customdried on vacuum

Sources & evidence

ORD record
ord-45469990c9eb495d9b1786a61e7f73e9
Source dataset
uspto-grants-2015_06
Patent number
US09056865B2

Reaction notes

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