Chloroacetyl chloride → tetrahydro-1-(5-trifluoromethyl-1,3,4-thiadiazol-2-yl)-3-methyl-6-chloroacetyloxy-2(1H)-pyrimidinone

HRID 435553Notes

Reaction equation

HRID 435553 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.C(N(CC)CC)C.[Cl:26][CH2:27][C:28](Cl)=[O:29]>C1C=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:28](=[O:29])[CH2:27][Cl:26])[CH2:12][CH2:11][N:10]([CH3:15])[C:9]2=[O:16])=[N:5][N:4]=1

Participants

5

Reactant 3

HCID 6577Chloroacetyl chlorideHCID 8471TriethylamineHCID 21400101tetrahydro-1-(5-trifluoromethyl-1,3,4-thiadiazol-2-yl)-3-methyl-6-hydroxy-2(1H)-pyrimidinone

Product 1

HCID 21455435tetrahydro-1-(5-trifluoromethyl-1,3,4-thiadiazol-2-yl)-3-methyl-6-chloroacetyloxy-2(1H)-pyrimidinone

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

Tetrahydro-1-(5-trifluoromethyl-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. Chloroacetyl 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 the desired product tetrahydro-1-(5-trifluoromethyl- 1,3,4-thiadiazol-2-yl)-3-methyl-6-chloroacetyloxy- 2(1H)-pyrimidinone as the residue.

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

Sources & evidence

ORD record
ord-adfdb575ef694f5e9fc84604872544d2
Source dataset
uspto-grants-1977_02
Patent number
US04006009

Reaction notes

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