2-Methylbenzenesulfonic acid → HCID 21501672, compound

HRID 1580014Notes

Reaction equation

HRID 1580014 reaction equation
[CH3:1][S:2]([C:4]1[S:8][C:7]([N:9]2[CH:14]([OH:15])[CH2:13][CH2:12][N:11]([CH2:16][C:17]#[CH:18])[C:10]2=[O:19])=[N:6][N:5]=1)=[O:3].[C:20]1(C)[C:21](S(O)(=O)=O)=[CH:22][CH:23]=[CH:24][CH:25]=1>C(O)CCCCC>[CH3:1][S:2]([C:4]1[S:8][C:7]([N:9]2[CH:14]([O:15][CH2:22][CH2:21][CH2:20][CH2:25][CH2:24][CH3:23])[CH2:13][CH2:12][N:11]([CH2:16][C:17]#[CH:18])[C:10]2=[O:19])=[N:6][N:5]=1)=[O:3]

Participants

4

Reactant 2

HCID 69252-Methylbenzenesulfonic acidHCID 21400073tetrahydro-1-(5-methylsulfinyl-1,3,4-thiadiazol-2-yl)-3-propargyl-6-hydroxy-2(1H)-pyrimidinone

Product 1

HCID 21501672HCID 21501672, compound

Reagents, catalysts & solvents 1

HCID 81031-HexanolSolvent

Procedure

Tetrahydro-1-(5-methylsulfinyl-1,3,4-thiadiazol-2-yl)-3-propargyl-6-hydroxy-2(1H)-pyrimidinone (7 grams), hexyl 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-methylsulfinyl-1,3,4-thiadiazol-2-yl)- 3-propargyl-6-hexyloxy-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-7df3f1d0b60c417296aaf1ceb44d52a2
Source dataset
uspto-grants-1976_01
Patent number
US03932410

Reaction notes

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