2-Methylbenzenesulfonic acid → HCID 21501676, compound

HRID 1288397Notes

Reaction equation

HRID 1288397 reaction equation
[CH2:1]([C:4]1[S:8][C:7]([N:9]2[CH:14]([OH:15])[CH2:13][CH2:12][N:11]([CH2:16][Cl:17])[C:10]2=[O:18])=[N:6][N:5]=1)[CH:2]=[CH2:3].[C:19]1(C)C(S(O)(=O)=O)=CC=CC=1>CO>[CH2:1]([C:4]1[S:8][C:7]([N:9]2[CH:14]([O:15][CH3:19])[CH2:13][CH2:12][N:11]([CH2:16][Cl:17])[C:10]2=[O:18])=[N:6][N:5]=1)[CH:2]=[CH2:3]

Participants

4

Reactant 2

HCID 69252-Methylbenzenesulfonic acidHCID 21501700HCID 21501700, compound

Product 1

HCID 21501676HCID 21501676, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Tetrahydro-1-(5-allyl-1,3,4-thiadiazol-2-yl)-3-chloromethyl-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-allyl-1,3,4-thiadiazol-2-yl)-3-chloromethyl-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-8d942b8bffab45538c7abc66c8b8c6fe
Source dataset
uspto-grants-1976_10
Patent number
US03988143

Reaction notes

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