Water → 2-heptylthio-6-methoxy-5H-1,3,4-thiadiazolo[3,2-a]pyrimidin-5-one

HRID 1073794Notes

Reaction equation

HRID 1073794 reaction equation
[NH2:1][C:2]1[S:3][C:4]([S:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14])=[N:5][N:6]=1.[OH:15][CH:16]=[C:17]([O:24][CH3:25])[C:18](OCCC)=O.O>C(Cl)(Cl)Cl>[CH2:8]([S:7][C:4]1[S:3][C:2]2=[N:1][CH:18]=[C:17]([O:24][CH3:25])[C:16](=[O:15])[N:6]2[N:5]=1)[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14]

Participants

5

Reactant 3

HCID 962WaterHCID 5344581,3,4-Thiadiazole, 2-amino-5-(heptylthio)-HCID 71336589Propyl 3-hydroxy-2-methoxyprop-2-enoate

Product 1

HCID 156107952-heptylthio-6-methoxy-5H-1,3,4-thiadiazolo[3,2-a]pyrimidin-5-oneYield 64%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A mixture of 4.7 g of 2-amino-5-heptylthio-1,3,4-thiadiazole, 3.3 g of propyl 3-hydroxy-2-methoxy-2-propenoate and 12 g of polyphosphoric acid was heated to 130°~135° C. and stirred for 30 minutes. After cooling, water and chloroform were added to the mixture and extraction was carried out. The organic layer was washed with a sodium hydrogen carbonate aqueous solution and water respectively, and dried over anhydrous sodium sulfate. The solvent was distilled off, and the residue was separated by silica gel column chromatography using an ethyl acetate/toluene mixture as an eluent. Thus 4.0 g of 2-heptylthio-6-methoxy-5H-1,3,4-thiadiazolo[3,2-a]pyrimidin-5-one was obtained. m.p. 68°~71° C. Yield 64%.

Workup

  1. temperaturewas heated to 130°~135° C.
  2. temperatureAfter cooling
  3. washThe organic layer was washed with a sodium hydrogen carbonate aqueous solution and water respectively
  4. dry with materialdried over anhydrous sodium sulfate
  5. distillationThe solvent was distilled off
  6. customthe residue was separated by silica gel column chromatography

Sources & evidence

ORD record
ord-3183bf8a420b4cbe81eb3c438a2e3056
Source dataset
uspto-grants-1990_11
Patent number
US04971971

Reaction notes

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