2-Methylbenzenesulfonic acid → tetrahydro-1-(5-methyl-1,3,4-thiadiazol-2-yl)-3-methyl-6-acetyloxy-2 (1H)-pyrimidinone

HRID 435522Notes

Reaction equation

HRID 435522 reaction equation
[CH3:1][C:2]1[S:6][C:5]([N:7]2[CH:12]([OH:13])[CH2:11][CH2:10][N:9]([CH3:14])[C:8]2=[O:15])=[N:4][N:3]=1.[C:16](OC(=O)C)(=[O:18])[CH3:17].C1(C)C(S(O)(=O)=O)=CC=CC=1>C1C=CC=CC=1>[CH3:1][C:2]1[S:6][C:5]([N:7]2[CH:12]([O:13][C:16](=[O:18])[CH3:17])[CH2:11][CH2:10][N:9]([CH3:14])[C:8]2=[O:15])=[N:4][N:3]=1

Participants

5

Reactant 3

HCID 69252-Methylbenzenesulfonic acidHCID 7918Acetic AnhydrideHCID 21400085Tetrahydro-1-(5-methyl-1,3,4-thiadiazol-2-yl)-3-methyl-6-hydroxy-2(1H)-pyrimidinone

Product 1

HCID 21455450tetrahydro-1-(5-methyl-1,3,4-thiadiazol-2-yl)-3-methyl-6-acetyloxy-2 (1H)-pyrimidinone

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

Tetrahydro-1-(5-methyl-1,3,4-thiadiazol-2-yl)-3-methyl-6-hydroxy-2 (1H)-pyrimidinone (0.1 mole), acetic anhydride (0.11 mole), toluenesulfonic acid (0.05 gram) and benzene (100 ml) are charged into a glass reaction vessel equipped with a mechanical stirrer and thermometer. The reaction mixture is heated on a steam bath with stirring for a period of about 2 hours. After this time the reaction mixture is cooled to room temperature and is stripped of solvent under reduced pressure leaving a residue. The residue is recrystallized to yield the desired product tetrahydro-1-(5-methyl-1,3,4-thiadiazol-2-yl)-3-methyl-6-acetyloxy-2 (1H)-pyrimidinone.

Workup

  1. customequipped with a mechanical stirrer
  2. temperatureThe reaction mixture is heated on a steam bath
  3. customleaving a residue
  4. customThe residue is recrystallized

Sources & evidence

ORD record
ord-8b9684425cd2491193b2e21f2ad282f5
Source dataset
uspto-grants-1977_02
Patent number
US04006009

Reaction notes

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