2-Methylbenzenesulfonic acid → HCID 21501681, compound

HRID 1288372Notes

Reaction equation

HRID 1288372 reaction equation
[CH3:1][S:2][C:3]1[S:7][C:6]([N:8]2[CH:13]([OH:14])[CH2:12][CH2:11][N:10]([CH2:15][CH2:16][CH3:17])[C:9]2=[O:18])=[N:5][N:4]=1.[C:19]1(C)[C:20](S(O)(=O)=O)=CC=C[CH:24]=1>C(O)CC>[CH3:1][S:2][C:3]1[S:7][C:6]([N:8]2[CH:13]([O:14][CH2:24][CH2:19][CH3:20])[CH2:12][CH2:11][N:10]([CH2:15][CH2:16][CH3:17])[C:9]2=[O:18])=[N:5][N:4]=1

Participants

4

Reactant 2

HCID 69252-Methylbenzenesulfonic acidHCID 21400080HCID 21400080, compound

Product 1

HCID 21501681HCID 21501681, compound

Reagents, catalysts & solvents 1

HCID 10311-PropanolSolvent

Procedure

Tetrahydro-1-(5-methylthio-1,3,4-thiadiazol-2-yl)-3-propyl-6-hydroxy-2(1H)-pyrimidinone (7 grams), propyl 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 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-methylthio-1,3,4-thiadiazol-2-yl)-3-propyl-6-propoxy-2(1H)-pyrimidinone.

Workup

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

Sources & evidence

ORD record
ord-962b29e014444577bbae41c7ca140715
Source dataset
uspto-grants-1976_10
Patent number
US03988143

Reaction notes

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