Triethylamine → HCID 21455415, compound

HRID 435547Notes

Reaction equation

HRID 435547 reaction equation
[F:1][C:2]([F:19])([F:18])[C:3]1[S:7][C:6]([N:8]2[CH:13]([OH:14])[CH2:12][CH2:11][N:10]([CH2:15][Cl:16])[C:9]2=[O:17])=[N:5][N:4]=1.C(N(CC)CC)C.[C:27](Cl)(=[O:33])[CH2:28][CH2:29][CH2:30][CH2:31][CH3:32]>C1C=CC=CC=1>[F:19][C:2]([F:1])([F:18])[C:3]1[S:7][C:6]([N:8]2[CH:13]([O:14][C:27](=[O:33])[CH2:28][CH2:29][CH2:30][CH2:31][CH3:32])[CH2:12][CH2:11][N:10]([CH2:15][Cl:16])[C:9]2=[O:17])=[N:5][N:4]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 67340Hexanoyl chlorideHCID 21455475HCID 21455475, compound

Product 1

HCID 21455415HCID 21455415, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

Tetrahydro-1-(5-trifluoromethyl-1,3,4-thiadiazol-2-yl)-3-chloromethyl-6-hydroxy-2(1H)-pyrimidinone (0.05 mole), triethylamine (0.06 mole) and benzene (50 ml) are charged into a glass reaction vessel equipped with a mechanical stirrer, thermometer and reflux condenser. Hexanoyl chloride (0.05 mole) is then added dropwise with stirring. After the addition is completed, the reaction mixture is heated at reflux with continued stirring for a period of about 30 minutes. After this time the reaction mixture is filtered and the filtrate is stripped of solvent under reduced pressure to yield a solid residue. The residue is recrystallized to yield the desired product tetrahydro-1-(5-trifluoromethyl- 1,3,4-thiadiazol-2-yl)-3-chloromethyl-6-hexanoyloxy-2(1H)-pyrimidinone.

Workup

  1. customequipped with a mechanical stirrer
  2. temperaturethermometer and reflux condenser
  3. additionAfter the addition
  4. temperaturethe reaction mixture is heated
  5. temperatureat reflux
  6. stirringwith continued stirring for a period of about 30 minutes
  7. filtrationAfter this time the reaction mixture is filtered
  8. customto yield a solid residue
  9. customThe residue is recrystallized

Sources & evidence

ORD record
ord-eb9ad41f727a492fb7db99abb71478fa
Source dataset
uspto-grants-1977_02
Patent number
US04006009

Reaction notes

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