2,6-Diethylbenzoyl chloride → N-[5-(1-ethyl-1-methylpropyl)-1,3,4-thiadiazol-2-yl]-2,6-diethylbenzamide

HRID 462363Notes

Reaction equation

HRID 462363 reaction equation
[NH2:1][C:2]1[S:3][C:4]([C:7]([CH2:11][CH3:12])([CH3:10])[CH2:8][CH3:9])=[N:5][N:6]=1.[CH2:13]([C:15]1[CH:23]=[CH:22][CH:21]=[C:20]([CH2:24][CH3:25])[C:16]=1[C:17](Cl)=[O:18])[CH3:14]>C1(C)C=CC=CC=1>[CH2:8]([C:7]([C:4]1[S:3][C:2]([NH:1][C:17](=[O:18])[C:16]2[C:20]([CH2:24][CH3:25])=[CH:21][CH:22]=[CH:23][C:15]=2[CH2:13][CH3:14])=[N:6][N:5]=1)([CH3:10])[CH2:11][CH3:12])[CH3:9]

Participants

4

Reactant 2

HCID 130685842,6-Diethylbenzoyl chlorideHCID 132342635-(3-Methylpentan-3-yl)-1,3,4-thiadiazol-2-amine

Product 1

HCID 13229314N-[5-(1-ethyl-1-methylpropyl)-1,3,4-thiadiazol-2-yl]-2,6-diethylbenzamideYield 36.2%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 1.85 g of 2-amino-5-(1-ethyl-1-methylpropyl)-1,3,4-thiadiazole and 2.21 g of 2,6-diethylbenzoyl chloride in 50 ml of toluene was heated at reflux for sixteen hours and then cooled and the solvent was removed by evaporation under reduced pressure to provide a solid residue. The solid was crystallized from 2B ethanol to give 1.25 g of N-[5-(1-ethyl-1-methylpropyl)-1,3,4-thiadiazol-2-yl]-2,6-diethylbenzamide.

Workup

  1. temperatureat reflux for sixteen hours
  2. temperaturecooled
  3. customthe solvent was removed by evaporation under reduced pressure
  4. customto provide a solid residue
  5. customThe solid was crystallized from 2B ethanol

Sources & evidence

ORD record
ord-353984fff6c2487db1640abca394abbe
Source dataset
uspto-grants-1985_05
Patent number
US04515625

Reaction notes

Loading…