Triethylamine → N-Ethenyl-5-ethoxy-3-oxo-1,2,4-thiadiazole-2(3H)-carboxamide

HRID 1833823Notes

Reaction equation

HRID 1833823 reaction equation
C(N(CC)CC)C.[OH:8][C:9]1[N:13]=[C:12]([O:14][CH2:15][CH3:16])[S:11][N:10]=1.[CH:17]([N:19]=[C:20]=[O:21])=[CH2:18]>C(OC(C)C)(C)C>[CH:17]([NH:19][C:20]([N:10]1[C:9](=[O:8])[N:13]=[C:12]([O:14][CH2:15][CH3:16])[S:11]1)=[O:21])=[CH2:18]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 77094Vinyl isocyanateHCID 178467476HCID 178467476, compound

Product 1

HCID 21387512N-Ethenyl-5-ethoxy-3-oxo-1,2,4-thiadiazole-2(3H)-carboxamideYield 69.8%

Reagents, catalysts & solvents 1

HCID 7914Diisopropyl EtherSolvent

Conditions

Temperature
20 °C

Procedure

1 ml of triethylamine was added to a solution of 14.6 g of 3-hydroxy-5-ethoxy-1,2,4-thiadiazole in 250 ml of isopropyl ether and after 5 minutes, 8 g of vinyl isocyanate were added. The mixture was stirred for 30 minutes at 20° C and was vacuum filtered and the recovered precipitate was washed, dried and crystallized from ethyl acetate to obtain 15 g of 2-(N-vinylcarbamoyl)-5-ethoxy-1,2,4-thiadiazole-3-one melting at 123° C.

Workup

  1. filtrationfiltered
  2. washthe recovered precipitate was washed
  3. customdried
  4. customcrystallized from ethyl acetate

Sources & evidence

ORD record
ord-916ac876808f43549d0b8f5cf3f1cd44
Source dataset
uspto-grants-1978_01
Patent number
US04067720

Reaction notes

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