2-Methylbenzenesulfonic acid → HCID 21501669, compound

HRID 1580001Notes

Reaction equation

HRID 1580001 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]1(C)C(S(O)(=O)=O)=CC=CC=1>CO>[CH3:1][C:2]1[S:6][C:5]([N:7]2[CH:12]([O:13][CH3:16])[CH2:11][CH2:10][N:9]([CH3:14])[C:8]2=[O:15])=[N:4][N:3]=1

Participants

4

Reactant 2

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

Product 1

HCID 21501669HCID 21501669, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Tetrahydro-1-(5-methyl-1,3,4-thiadiazol-2-yl)-3-methyl-6-hydroxy-2(1H)-pyrimidinone (7 grams), methyl alcohol (50 ml) and toluenesulfonic acid (0.2 grams) are charged into a glass reaction vessel equipped with a mechanical stirrer, thermometer and reflux condenser. The reaction mixture is then heated at reflux for a period of about 24 hours. After this time the mixture is stripped of unreacted alcohol under reduced pressure to yield a solid product. This product is then recrystallized to yield the desired product tetrahydro-1-(5-methyl-1,3,4-thiadiazol-2-yl)-3-methyl-6-methoxy-2(1H)-pyrimidinone.

Workup

  1. customequipped with a mechanical stirrer
  2. temperaturethermometer and reflux condenser
  3. temperatureThe reaction mixture is then heated
  4. temperatureat reflux for a period of about 24 hours
  5. customto yield a solid product
  6. customThis product is then recrystallized

Sources & evidence

ORD record
ord-780bccd5c85c4e3ca767de021100d32a
Source dataset
uspto-grants-1976_01
Patent number
US03932410

Reaction notes

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