Triethyl orthoacetate → N-(1-Ethoxyethylidene)-3-(2-chlorophenyl)-1,2,4-thiadiazole-5-sulfonamide

HRID 704027Notes

Reaction equation

HRID 704027 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[N:12]=[C:11]([S:13]([NH2:16])(=[O:15])=[O:14])[S:10][N:9]=1.[C:17](OCC)(OCC)([O:19][CH2:20][CH3:21])[CH3:18]>>[CH2:17]([O:19][C:20](=[N:16][S:13]([C:11]1[S:10][N:9]=[C:8]([C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=2[Cl:1])[N:12]=1)(=[O:14])=[O:15])[CH3:21])[CH3:18]

Participants

3

Reactant 2

HCID 66221Triethyl orthoacetateHCID 141831363-(2-Chlorophenyl)-1,2,4-thiadiazole-5-sulfonamide

Product 1

HCID 53969492N-(1-Ethoxyethylidene)-3-(2-chlorophenyl)-1,2,4-thiadiazole-5-sulfonamide

Procedure

A mixture of 3 g of 3-(2-chlorophenyl)-1,2,4-thiadiazole-5-sulfonamide and 11 ml of triethyl orthoacetate was warmed to reflux for 3.5 hours. The mixture was cooled, triturated with hexane (25 ml) and filtered to give 3.13 g of solid, m.p. 70°-72° C.

Workup

  1. temperaturewas warmed
  2. temperatureto reflux for 3.5 hours
  3. temperatureThe mixture was cooled
  4. customtriturated with hexane (25 ml)
  5. filtrationfiltered

Sources & evidence

ORD record
ord-a42e33385da44cfda072cdaffcbcfedf
Source dataset
uspto-grants-1991_01
Patent number
US04985450

Reaction notes

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