Pyridine → HCID 21404041, compound

HRID 1605897Notes

Reaction equation

HRID 1605897 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.[CH3:19][N:20]([C:24]1[CH:29]=[CH:28][CH:27]=[C:26]([CH2:30][Cl:31])[CH:25]=1)[C:21](Cl)=[O:22].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:21](=[O:22])[N:20]([CH3:19])[C:24]3[CH:29]=[CH:28][CH:27]=[C:26]([CH2:30][Cl:31])[CH:25]=3)[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 21404029HCID 21404029, compound

Product 1

HCID 21404041HCID 21404041, compound

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-methyl-N-(3-chloromethylphenyl)carbamoyl 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 recrysallized to yield the desired product tetrahydro-1-(5-trifluoromethyl-1,3,4-thiadiazol-2-yl)-3-methyl-6-[N-methyl-N-(3-chloromethylphenyl)carbamoyloxy]-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

Sources & evidence

ORD record
ord-eee255e24a244bb8aff5e19de635fa66
Source dataset
uspto-grants-1976_04
Patent number
US03951976

Reaction notes

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