Methanol → HCID 15610802, compound

HRID 1073799Notes

Reaction equation

HRID 1073799 reaction equation
[CH3:1][OH:2].Cl[C:4]1[N:5]=[C:6]2[S:16][C:15]([S:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])=[N:14][N:7]2[C:8](=[O:13])[C:9]=1[N+:10]([O-:12])=[O:11].N1C=CC=CC=1>O>[CH2:18]([S:17][C:15]1[S:16][C:6]2=[N:5][C:4]([O:2][CH3:1])=[C:9]([N+:10]([O-:12])=[O:11])[C:8](=[O:13])[N:7]2[N:14]=1)[CH2:19][CH2:20][CH2:21][CH2:22][CH3:23]

Participants

5

Reactant 3

HCID 887MethanolHCID 1049PyridineHCID 15610801HCID 15610801, compound

Product 1

HCID 15610802HCID 15610802, compoundYield 63%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To 50 ml of methanol, 3.0 g of 7-chloro-2-hexylthio-6-nitro-5H-1,3,4-thiadiazolo[3,2-a]pyrimidin-5-one and 1.0 g of pyridine were added, and the mixture was stirred under refluxing for 30 minutes. Water was added to the reaction mixture and the organic layer was extracted with ethyl acetate The ethyl acetate solution was dried over anhydrous magnesium sulfate, and the solvent was distilled off. The residue was purified by silica gel column chromatography using an ethyl acetate/hexane mixture as an eluent. Thus 1.9 g of brown transparent viscous liquid of 2-hexylthio-7-methoxy-6-nitro-5H-1,3,4-thiadiazolo[3,2-a]pyrimidin-5-one was obtained. Yield 63%.

Workup

  1. temperatureunder refluxing for 30 minutes
  2. extractionthe organic layer was extracted with ethyl acetate The ethyl acetate solution
  3. dry with materialwas dried over anhydrous magnesium sulfate
  4. distillationthe solvent was distilled off
  5. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-1f14e3809a6f42a3b6c7feefca3c3335
Source dataset
uspto-grants-1990_11
Patent number
US04971971

Reaction notes

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