Ethyl 3-ethoxy-2-propenoate → 2-heptylthio-5H-1,3,4-thiadiazolo[3,2-a]pyrimidin-5-one

HRID 1607552Notes

Reaction equation

HRID 1607552 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.C([O:17][CH:18]=[CH:19][C:20](OCC)=O)C>>[CH2:8]([S:7][C:4]1[S:3][C:2]2=[N:1][CH:20]=[CH:19][C:18](=[O:17])[N:6]2[N:5]=1)[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14]

Participants

3

Reactant 2

HCID 221780Ethyl 3-ethoxy-2-propenoateHCID 5344581,3,4-Thiadiazole, 2-amino-5-(heptylthio)-

Product 1

HCID 156107962-heptylthio-5H-1,3,4-thiadiazolo[3,2-a]pyrimidin-5-oneYield 51.2%

Procedure

A mixture of 20.1 g of 2-amino-5-heptylthio-1,3,4-thiadiazole, 20.0 g of ethyl 3-ethoxypropenoate and 23 g of polyphosphoric acid was heated to 130°~140° C. and stirred for 30 minutes. The residue obtained by the same procedure as in Preparation Example 13 was purified by silica gel column chromatography using an ethyl acetate/toluene mixture as an eluent. Thus 12.6 g of 2-heptylthio-5H-1,3,4-thiadiazolo[3,2-a]pyrimidin-5-one was obtained.

Workup

  1. temperaturewas heated to 130°~140° C.
  2. customThe residue obtained by the same procedure as in Preparation Example 13
  3. customwas purified by silica gel column chromatography

Sources & evidence

ORD record
ord-8785c7d28d0347c08a60192177a3c52c
Source dataset
uspto-grants-1989_09
Patent number
US04866064

Reaction notes

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