2-Methylbenzenesulfonic acid → tetrahydro-1-(5-methoxy-1,3,4-thiadiazol-2-yl)-3-but-3-enyl-6-ethoxy-2(1H)-pyrimidinone

HRID 1288390Notes

Reaction equation

HRID 1288390 reaction equation
[CH3:1][O: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][CH:17]=[CH2:18])[C:9]2=[O:19])=[N:5][N:4]=1.[C:20]1(C)C(S(O)(=O)=O)=CC=C[CH:25]=1>C(O)C>[CH3:1][O:2][C:3]1[S:7][C:6]([N:8]2[CH:13]([O:14][CH2:20][CH3:25])[CH2:12][CH2:11][N:10]([CH2:15][CH2:16][CH:17]=[CH2:18])[C:9]2=[O:19])=[N:5][N:4]=1

Participants

4

Reactant 2

HCID 69252-Methylbenzenesulfonic acidHCID 21400096tetrahydro-1-(5-methoxy-1,3,4-thiadiazol-2-yl)-3-but-3-enyl-6-hydroxy-2(1H)-pyrimidinone

Product 1

HCID 21501674tetrahydro-1-(5-methoxy-1,3,4-thiadiazol-2-yl)-3-but-3-enyl-6-ethoxy-2(1H)-pyrimidinone

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Tetrahydro-1-(5-methoxy-1,3,4-thiadiazol-2-yl)-3-but-3-enyl-6-hydroxy-2(1H)-pyrimidinone (7 grams), ethyl alcohol (50 ml) and toluenesulfonic acid (0.2 grams) are charged into a glass reaction vessel equipped with a mechanical stirrer, thermomater 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-methoxy-1,3,4-thiadiazol-2-yl)-3-but-3-enyl-6 -ethoxy-2(1H)-pyrimidinone.

Workup

  1. customequipped with a mechanical stirrer
  2. temperaturethermomater 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-b852197552c748eb9af8e3a73fc85e64
Source dataset
uspto-grants-1976_10
Patent number
US03988143

Reaction notes

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