Benzoyl chloride → HCID 21481861, compound

HRID 1415369Notes

Reaction equation

HRID 1415369 reaction equation
[CH:1]1([C:7]2[S:11][C:10]([N:12]3[CH:17]([OH:18])[CH2:16][CH2:15][N:14]([CH3:19])[C:13]3=[O:20])=[N:9][N:8]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C(N(CC)CC)C.[C:28](Cl)(=[O:35])[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1>C1C=CC=CC=1>[CH:1]1([C:7]2[S:11][C:10]([N:12]3[CH:17]([O:18][C:28](=[O:35])[C:29]4[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=4)[CH2:16][CH2:15][N:14]([CH3:19])[C:13]3=[O:20])=[N:9][N:8]=2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

5

Reactant 3

HCID 7412Benzoyl chlorideHCID 8471TriethylamineHCID 21481855HCID 21481855, compound

Product 1

HCID 21481861HCID 21481861, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

Tetrahydro-1-(5-cyclohexyl-1,3,4-thiadiazol-2-yl)-3-methyl-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. Benzoyl 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 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-cyclohexyl-1,3,4-thiadiazol-2-yl)-3-methyl-6-benzoyloxy-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 is filtered
  8. customto yield a solid residue
  9. customThe residue is recrystallized

Sources & evidence

ORD record
ord-a78f8fd8f9ee4229978765c38fb4e576
Source dataset
uspto-grants-1977_01
Patent number
US04004912

Reaction notes

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