2,6-Dimethoxybenzoyl chloride → N-[5-(1,3-Dithian-2-yl)-1,3,4-thiadiazol-2-yl]-2,6-dimethoxybenzamide

HRID 980114Notes

Reaction equation

HRID 980114 reaction equation
[CH3:1][O:2][C:3]1[CH:11]=[CH:10][CH:9]=[C:8]([O:12][CH3:13])[C:4]=1[C:5](Cl)=[O:6].[NH2:14][C:15]1[S:16][C:17]([CH:20]2[S:25][CH2:24][CH2:23][CH2:22][S:21]2)=[N:18][N:19]=1>C1(C)C=CC=CC=1>[S:21]1[CH2:22][CH2:23][CH2:24][S:25][CH:20]1[C:17]1[S:16][C:15]([NH:14][C:5](=[O:6])[C:4]2[C:3]([O:2][CH3:1])=[CH:11][CH:10]=[CH:9][C:8]=2[O:12][CH3:13])=[N:19][N:18]=1

Participants

4

Reactant 2

HCID 748102,6-Dimethoxybenzoyl chlorideHCID 199118695-(1,3-Dithian-2-yl)-1,3,4-thiadiazol-2-amine

Product 1

HCID 13239361N-[5-(1,3-Dithian-2-yl)-1,3,4-thiadiazol-2-yl]-2,6-dimethoxybenzamideYield 60%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 1.0 g. of 2,6-dimethoxybenzoyl chloride and 1.1 g of 2-amino-5-(1,3-dithian-2-yl)-1,3,4-thiadiazole in 20 ml of toluene was heated at reflux for eighteen hours under a nitrogen atmosphere. The reaction mixture was cooled to room temperature and the solvent was removed by evaporation under reduced pressure to provide a white solid. The solid was chromatographed over silica gel to provide 1.2 g (60% yield) of N-[5-(1,3-dithian-2-yl)-1,3,4-thiadiazol-2-yl]-2,6-dimethoxybenzamide.

Workup

  1. temperatureat reflux for eighteen hours under a nitrogen atmosphere
  2. customthe solvent was removed by evaporation under reduced pressure
  3. customto provide a white solid
  4. customThe solid was chromatographed over silica gel

Sources & evidence

ORD record
ord-2161d7cd96fb427ca5dd7d1faf8460c1
Source dataset
uspto-grants-1987_01
Patent number
US04636243

Reaction notes

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