2-Methylbenzenesulfonic acid → HCID 21501686, compound

HRID 1288386Notes

Reaction equation

HRID 1288386 reaction equation
[C:1]([C:5]1[S:9][C:8]([N:10]2[CH:15]([OH:16])[CH2:14][CH2:13][N:12]([CH3:17])[C:11]2=[O:18])=[N:7][N:6]=1)([CH3:4])([CH3:3])[CH3:2].[C:19]1(C)C(S(O)(=O)=O)=CC=CC=1>CO>[C:1]([C:5]1[S:9][C:8]([N:10]2[CH:15]([O:16][CH3:19])[CH2:14][CH2:13][N:12]([CH3:17])[C:11]2=[O:18])=[N:7][N:6]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 69252-Methylbenzenesulfonic acidHCID 21400082tetrahydro-1-(5-t-butyl-1,3,4-thiadiazol-2-yl)-3-methyl-6-hydroxy-2(1H)-pyrimidinone

Product 1

HCID 21501686HCID 21501686, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Tetrahydro-1-(5-t-butyl-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-t-butyl-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-2e8b1645cc4c44fda1612e01fad03160
Source dataset
uspto-grants-1976_10
Patent number
US03988143

Reaction notes

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