Pyridine → tetrahydro-1-(5-trifluoromethyl-1,3,4-thiadiazol-2-yl)-3-methyl-6-(N-hexyl-N-methylcarbamoyloxy)-2(1H)-pyrimidinone

HRID 972420Notes

Reaction equation

HRID 972420 reaction equation
[F:1][C:2]([F:18])([F:17])[C:3]1[S:7][C:6]([N:8]2[CH:13]([OH:14])[CH2:12][CH2:11][N:10]([CH3:15])[C:9]2=[O:16])=[N:5][N:4]=1.[CH2:19]([N:25]([CH3:29])[C:26](Cl)=[O:27])[CH2:20][CH2:21][CH2:22][CH2:23][CH3:24].N1C=CC=CC=1>C1(C)C=CC=CC=1>[F:18][C:2]([F:1])([F:17])[C:3]1[S:7][C:6]([N:8]2[CH:13]([O:14][C:26](=[O:27])[N:25]([CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])[CH3:29])[CH2:12][CH2:11][N:10]([CH3:15])[C:9]2=[O:16])=[N:5][N:4]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 21400101tetrahydro-1-(5-trifluoromethyl-1,3,4-thiadiazol-2-yl)-3-methyl-6-hydroxy-2(1H)-pyrimidinoneHCID 23509235N-hexyl-N-methylcarbamoyl chloride

Product 1

HCID 21404019tetrahydro-1-(5-trifluoromethyl-1,3,4-thiadiazol-2-yl)-3-methyl-6-(N-hexyl-N-methylcarbamoyloxy)-2(1H)-pyrimidinone

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Tetrahydro-1-(5-trifluoromethyl-1,3,4-thiadiazol-2-yl)-3-methyl-6-hydroxy-2(1H)-pyrimidinone (0.05 mole), N-hexyl-N-methylcarbamoyl chloride (0.06 mole), pyridine (0.06 mole) and toluene (150 ml) are charged into a glass reaction vessel equipped with a mechanical stirrer, thermometer and reflux condenser. The reaction mixture is heated at reflux with stirring for a period of about 3 hours. After this time the reaction mixture is cooled to room temperature and is filtered to remove pyridine hydrochloride. The filtrate is then washed with water, dried over anhydrous magnesium sulfate and stripped of solvent leaving a residue. The residue is recrystallized to yield the desired product tetrahydro-1-(5-trifluoromethyl-1,3,4-thiadiazol-2-yl)-3-methyl-6-(N-hexyl-N-methylcarbamoyloxy)-2(1H)-pyrimidinone.

Workup

  1. customequipped with a mechanical stirrer
  2. temperaturethermometer and reflux condenser
  3. temperatureThe reaction mixture is heated
  4. temperatureat reflux
  5. filtrationis filtered
  6. customto remove pyridine hydrochloride
  7. washThe filtrate is then washed with water
  8. dry with materialdried over anhydrous magnesium sulfate
  9. customleaving a residue
  10. customThe residue is recrystallized

Sources & evidence

ORD record
ord-01a04d0c169b48eea0fd61c0efc64e44
Source dataset
uspto-grants-1977_10
Patent number
US04053298

Reaction notes

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