2-Methylbenzenesulfonic acid → HCID 21481868, compound

HRID 1415354Notes

Reaction equation

HRID 1415354 reaction equation
[CH:1]1([C:4]2[S:8][C:7]([N:9]3[CH:14]([OH:15])[CH2:13][CH2:12][N:11]([CH3:16])[C:10]3=[O:17])=[N:6][N:5]=2)[CH2:3][CH2:2]1.[C:18](OC(=O)C)(=[O:20])[CH3:19].C1(C)C(S(O)(=O)=O)=CC=CC=1>C1C=CC=CC=1>[CH:1]1([C:4]2[S:8][C:7]([N:9]3[CH:14]([O:15][C:18](=[O:20])[CH3:19])[CH2:13][CH2:12][N:11]([CH3:16])[C:10]3=[O:17])=[N:6][N:5]=2)[CH2:2][CH2:3]1

Participants

5

Reactant 3

HCID 69252-Methylbenzenesulfonic acidHCID 7918Acetic AnhydrideHCID 21418670tetrahydro-1-(5-cyclopropyl-1,3,4-thiadiazol-2-yl)-3-methyl-6-hydroxy-2(1H)-pyrimidinone

Product 1

HCID 21481868HCID 21481868, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

Tetrahydro-1-(5-cyclopropyl-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-cyclopropyl-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-0037483b9fe342d58e3c8349d2d0d24b
Source dataset
uspto-grants-1977_01
Patent number
US04004912

Reaction notes

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