Triethylamine → tetrahydro-1-(5-t-butyl-1,3,4-thiadiazol-2-yl)-3-methyl-6-[alpha-(3,5-dinitrophenyl)acetyloxy]-2 (1H)-pyrimidinone

HRID 435550Notes

Reaction equation

HRID 435550 reaction equation
[C:1]([C:5]1[S:9][C:8]([N:10]2[CH:15]([OH:16])[CH2:14][CH2:13][N:12]([CH3:17])[C:11]2=[O:18])=[N:7][N:6]=1)([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.[N+:26]([C:29]1[CH:30]=[C:31]([CH2:38][C:39](Cl)=[O:40])[CH:32]=[C:33]([N+:35]([O-:37])=[O:36])[CH:34]=1)([O-:28])=[O:27]>C1C=CC=CC=1>[C:1]([C:5]1[S:9][C:8]([N:10]2[CH:15]([O:16][C:39](=[O:40])[CH2:38][C:31]3[CH:30]=[C:29]([N+:26]([O-:28])=[O:27])[CH:34]=[C:33]([N+:35]([O-:37])=[O:36])[CH:32]=3)[CH2:14][CH2:13][N:12]([CH3:17])[C:11]2=[O:18])=[N:7][N:6]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 21400082tetrahydro-1-(5-t-butyl-1,3,4-thiadiazol-2-yl)-3-methyl-6-hydroxy-2(1H)-pyrimidinoneHCID 21455466alpha-(3,5-Dinitrophenyl)acetyl chloride

Product 1

HCID 21455436tetrahydro-1-(5-t-butyl-1,3,4-thiadiazol-2-yl)-3-methyl-6-[alpha-(3,5-dinitrophenyl)acetyloxy]-2 (1H)-pyrimidinone

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

Tetrahydro-1-(5-t-butyl-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. α-(3,5-Dinitrophenyl)acetyl 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-t-butyl-1,3,4-thiadiazol-2-yl)-3-methyl-6-[α-(3,5 -dinitrophenyl)acetyloxy] -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-68d4dcd6d3da4fe0bc697d8ab6f2c33f
Source dataset
uspto-grants-1977_02
Patent number
US04006009

Reaction notes

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