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

HRID 2292304Notes

Reaction equation

HRID 2292304 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]([C:20]([CH2:23][O:24][C:25](=[O:31])[CH2:26][O:27][C:28](=[O:30])[CH3:29])([CH3:22])[CH3:21])=[N:18][N:19]=1>C1(C)C=CC=CC=1.CCCCC>[C:28]([O:27][CH2:26][C:25]([O:24][CH2:23][C:20]([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)([CH3:22])[CH3:21])=[O:31])(=[O:30])[CH3:29]

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 19911975N-[5-((2-acetoxy-1-acetoxymethyl)-1-methylethyl)-1,3,4-thiadiazol-2-yl]-2,6-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-97c6f6d587034858add91e4a6e799816
Source dataset
uspto-grants-1989_01
Patent number
US04801718

Reaction notes

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