Propionyl chloride → HCID 13655523, compound

HRID 1380787Notes

Reaction equation

HRID 1380787 reaction equation
[N:1]1([CH:6]([CH:14]([OH:23])[C:15]2[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][C:16]=2[Cl:22])[C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[CH:5]=[N:4][CH:3]=[N:2]1.[C:24](Cl)(=[O:27])[CH2:25][CH3:26]>CN(C)C1C=CN=CC=1.C(Cl)(Cl)Cl>[C:10]([O:9][C:7](=[O:8])[CH:6]([N:1]1[CH:5]=[N:4][CH:3]=[N:2]1)[CH:14]([O:23][C:24](=[O:27])[CH2:25][CH3:26])[C:15]1[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][C:16]=1[Cl:22])([CH3:13])([CH3:11])[CH3:12]

Participants

5

Reactant 2

HCID 62324Propionyl chlorideHCID 13655522HCID 13655522, compound

Product 1

HCID 13655523HCID 13655523, compoundYield 76.3%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6212ChloroformSolvent

Procedure

3.15 gms of t-butyl α-(1,2,4-triazol-1-yl)-β-hydroxy-β-(2,4-dichlorophenyl)propionate were added to 50 mls of chloroform along with 1.1 gms of 4-dimethylaminopyridine. 1.25 gms of propionyl chloride were then added to the system. The reaction mixture was then refluxed for 18 hours. The reaction solution was then first washed with aqueous 5 wt. % hydrochloric acid and then with aqueous sodium hydroxide. The organic phase was dried over sodium sulfate and then filtered. The filtrate was evaporated to dryness under vacuum affording 2.78 gms of the title compound as a yellow wax.

Workup

  1. temperatureThe reaction mixture was then refluxed for 18 hours
  2. washThe reaction solution was then first washed with aqueous 5 wt. % hydrochloric acid
  3. dry with materialThe organic phase was dried over sodium sulfate
  4. filtrationfiltered
  5. customThe filtrate was evaporated to dryness under vacuum

Sources & evidence

ORD record
ord-8846728798794fda86a75a75c90fc35e
Source dataset
uspto-grants-1986_04
Patent number
US04584008

Reaction notes

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