Azane;hydrate → 3-Chloro-4,5-dipropargyloxybenzamide

HRID 1708978Notes

Reaction equation

HRID 1708978 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([O:15][CH2:16][C:17]#[CH:18])[C:10]=1[O:11][CH2:12][C:13]#[CH:14])[C:5](Cl)=[O:6].O.[NH3:20]>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([O:15][CH2:16][C:17]#[CH:18])[C:10]=1[O:11][CH2:12][C:13]#[CH:14])[C:5]([NH2:20])=[O:6]

Participants

4

Reactant 2

HCID 12896473Azane;hydrateHCID 14774344HCID 14774344, compound

Product 1

HCID 141303293-Chloro-4,5-dipropargyloxybenzamide

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 3-choro-4,5-dipropargyloxybenzoyl chloride (1.00 g) in 30% ammonia water (20 ml) and toluene (10 ml) was stirred under reflux for 10 minutes, poured into ice-water and extracted with ethyl acetate. The extract was washed with water, dried over magnesium sulfate and concentrated under reduced pressure to give a residue. The residue was further washed with hexane to give 3-chloro-4,5-dipropargyloxybenzamide (0.88 g). m.p. 122°-125° C.

Workup

  1. temperatureunder reflux for 10 minutes
  2. extractionextracted with ethyl acetate
  3. washThe extract was washed with water
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customto give a residue
  7. washThe residue was further washed with hexane

Sources & evidence

ORD record
ord-a7b64744d83d465cb79c24a9e649dbed
Source dataset
uspto-grants-1990_08
Patent number
US04946865

Reaction notes

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