Benzene, 1-chloro-3-isocyanato- → HCID 21387491, compound

HRID 1833801Notes

Reaction equation

HRID 1833801 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([N:8]=[C:9]=[O:10])[CH:5]=[CH:6][CH:7]=1.[OH:11][C:12]1[N:16]=[C:15]([O:17][CH2:18][CH3:19])[S:14][N:13]=1>O1CCCC1>[Cl:1][C:2]1[CH:3]=[C:4]([NH:8][C:9]([N:13]2[C:12](=[O:11])[N:16]=[C:15]([O:17][CH2:18][CH3:19])[S:14]2)=[O:10])[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 17968Benzene, 1-chloro-3-isocyanato-HCID 178467476HCID 178467476, compound

Product 1

HCID 21387491HCID 21387491, compoundYield 43.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
20 °C

Procedure

43 g of 3-chlorophenyl isocyanate were added to a solution of 29.4 g of 3-hydroxy-5-ethoxy-1,2,4-thiadiazole in 300 ml of tetrahydrofuran and the mixture was stirred for 21/2 hours at 20° C. The mixture was evaporated to dryness under reduced pressure and the residue was crystallized from ethyl acetate to obtain 26 g of 2-(N-m-chlorophenylcarbamoyl)-5-ethoxy-1,2,4-thiadiazole-3-one melting at 141° C.

Workup

  1. customThe mixture was evaporated to dryness under reduced pressure
  2. customthe residue was crystallized from ethyl acetate

Sources & evidence

ORD record
ord-10b9ef064c8b4085b486a5f73a7c8f14
Source dataset
uspto-grants-1978_01
Patent number
US04067720

Reaction notes

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