Acetic Anhydride → N-(4-Chlorobut-2-yn-1-yl)acetamide

HRID 2188220Notes

Reaction equation

HRID 2188220 reaction equation
Cl.[NH2:2][CH2:3][C:4]#[C:5][CH2:6][Cl:7].[C:8](OCC)(=[O:10])[CH3:9].C(OC(=O)C)(=O)C>C([O-])(=O)C.[Na+]>[C:8]([NH:2][CH2:3][C:4]#[C:5][CH2:6][Cl:7])(=[O:10])[CH3:9]

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 8857Ethyl AcetateHCID 27951244-chlorobut-2-yn-1-amine Hydrochloride

Product 1

HCID 15177015N-(4-Chlorobut-2-yn-1-yl)acetamide

Reagents, catalysts & solvents 1

HCID 517045Sodium AcetateSolvent2×

Procedure

1-Amino-4-chloro-2-butyne hydrochloride (59.75 g) was dissolved in 10% aqueous sodium acetate-solution (335 ml). Ethyl acetate (500 ml) was added, and acetic anhydride (70 ml) was added dropwise at room temperature. A 25% aqueous sodium acetate solution was added to pH 5 and the solution was stirred for 30 min at room temperature. The ethyl acetate layer was separated, and the aqueous layer was extracted twice with ethyl acetate. The combined organic layers were washed with water, brine and dried over sodium sulphate, filtered and evaporated in vacuo yielding 1-acetylamino4-chloro-2-butyne as a yellow syrup (58.8 g).

Workup

  1. customThe ethyl acetate layer was separated
  2. extractionthe aqueous layer was extracted twice with ethyl acetate
  3. washThe combined organic layers were washed with water, brine
  4. dry with materialdried over sodium sulphate
  5. filtrationfiltered
  6. customevaporated in vacuo

Sources & evidence

ORD record
ord-063e5357311f47758bf47e6b41212a95
Source dataset
uspto-grants-2002_06
Patent number
US06410684B1

Reaction notes

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