HCID 12401740, compound → HCID 21387513, compound

HRID 1833804Notes

Reaction equation

HRID 1833804 reaction equation
[Cl:1][C:2]([N:6]=[C:7]=[O:8])=[C:3]([Cl:5])[Cl:4].[OH:9][C:10]1[N:14]=[C:13]([O:15][CH2:16][CH3:17])[S:12][N:11]=1>C1C=CC=CC=1>[Cl:1][C:2]([NH:6][C:7]([N:11]1[C:10](=[O:9])[N:14]=[C:13]([O:15][CH2:16][CH3:17])[S:12]1)=[O:8])=[C:3]([Cl:5])[Cl:4]

Participants

4

Reactant 2

HCID 12401740HCID 12401740, compoundHCID 178467476HCID 178467476, compound

Product 1

HCID 21387513HCID 21387513, compoundYield 46.1%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Conditions

Temperature
20 °C

Procedure

51.7 g of trichlorovinyl isocyanate were added dropwise to a solution of 21.9 g of 3-hydroxy-5-ethoxy-1,2,4-thiadiazole in 300 ml of benzene and after stirring the mixture for 16 hours at 20° C, the mixture was filtered. The filtrate was evaporated to dryness and the product was eluted with 7-3 benzene-ethyl acetate mixture and crystallized from isopropyl ether to obtain 22 g of 2-(N-trichlorovinylcarbamoyl)-5-ethoxy-1,2,4-thiadiazole-3-one melting at 123° C.

Workup

  1. filtrationthe mixture was filtered
  2. customThe filtrate was evaporated to dryness
  3. washthe product was eluted with 7-3 benzene-ethyl acetate mixture
  4. customcrystallized from isopropyl ether

Sources & evidence

ORD record
ord-dc9b202ab6614c6cbafd8b34153481ea
Source dataset
uspto-grants-1978_01
Patent number
US04067720

Reaction notes

Loading…