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

HRID 1833805Notes

Reaction equation

HRID 1833805 reaction equation
[Cl:1][CH2:2][C:3]([N:5]=[C:6]=[O:7])=[O:4].[OH:8][C:9]1[N:13]=[C:12]([O:14][CH2:15][CH3:16])[S:11][N:10]=1>C1C=CC=CC=1>[Cl:1][CH2:2][C:3]([NH:5][C:6]([N:10]1[C:9](=[O:8])[N:13]=[C:12]([O:14][CH2:15][CH3:16])[S:11]1)=[O:7])=[O:4]

Participants

4

Reactant 2

HCID 78209Chloroacetyl isocyanateHCID 178467476HCID 178467476, compound

Product 1

HCID 21387509N-(Chloroacetyl)-5-ethoxy-3-oxo-1,2,4-thiadiazole-2(3H)-carboxamideYield 58%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Conditions

Temperature
20 °C

Procedure

31.5 g of α-chloroacetyl isocyanate were added dropwise to a solution of 18.98 g of 3-hydroxy-5-ethoxy-1,2,4-thiadiazole in 200 ml of benzene and after stirring the mixture for 17 hours at 20° C, it was vacuum filtered. The recovered crystals were dried to obtain 20 g of 2-(N-α-chloroacetylcarbamoyl)-5-ethoxy-1,2,4-thiadiazole-3-one melting at 132° C.

Workup

  1. filtrationfiltered
  2. customThe recovered crystals were dried

Sources & evidence

ORD record
ord-abec7180f484464fbcf5172e68d0501e
Source dataset
uspto-grants-1978_01
Patent number
US04067720

Reaction notes

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