2,6-Dimethoxybenzoyl chloride → 2,6-DIMETHOXYBENZAMIDE

HRID 1649323Notes

Reaction equation

HRID 1649323 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]C1SC(C(COC(=O)COC(=O)C)(C)C)=NN=1>C1(C)C=CC=CC=1.CCCCC>[CH3:1][O:2][C:3]1[CH:11]=[CH:10][CH:9]=[C:8]([O:12][CH3:13])[C:4]=1[C:5]([NH2:14])=[O:6]

Participants

5

Reactant 2

HCID 748102,6-Dimethoxybenzoyl chlorideHCID 199119102-Amino-5-[(2-acetoxy-1-acetoxymethyl)-1-methylethyl]-1,3,4-thiadiazole

Product 1

HCID 890782,6-DIMETHOXYBENZAMIDEYield 3%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8003PentaneSolvent

Procedure

A solution of 300 mg of 2,6-dimethoxybenzoyl chloride in 20 ml of toluene containing 300 mg of 2-amino-5-[(2-acetoxy-1-acetoxymethyl)-1-methylethyl]-1,3,4-thiadiazole was heated at reflux for eighteen hours. The reaction mixture was cooled to room temperature and diluted with pentane. A solid precipitate which formed was collected by filtration and air dried to give N-[5-(2-acetoxy-1-acetoxymethyl)-1-methylethyl)-1,3,4-thiadiazol-2-yl]-2,6-dimethoxybenzamide in 3% yield.

Workup

  1. temperatureat reflux for eighteen hours
  2. customA solid precipitate which formed
  3. filtrationwas collected by filtration and air
  4. customdried

Sources & evidence

ORD record
ord-67d9835a33594db09d8a6f8448eb746d
Source dataset
uspto-grants-1983_11
Patent number
US04416683

Reaction notes

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