Chloroacetyl chloride → HCID 12945647, compound

HRID 1112732Notes

Reaction equation

HRID 1112732 reaction equation
[Cl:1][CH2:2][C:3](Cl)=[O:4].Cl.[CH2:7]([NH2:16])[C:8]([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)=[O:9]>CN(C)C=O>[CH2:7]([NH:16][C:3](=[O:4])[CH2:2][Cl:1])[C:8]([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)=[O:9]

Participants

4

Reactant 2

HCID 6577Chloroacetyl chlorideHCID 2723597Ethanone, 2-amino-1-phenyl-, hydrochloride (1:1)

Product 1

HCID 12945647HCID 12945647, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Chloroacetyl chloride (25 g; 0.226 mole) was added slowly to a stirred solution of phenacylamine hydrochloride (25.9 g; 0.151 mole) in anhydrous dimethylformamide (DMF) (80 ml) at room temperature. The internal temperature rose to ca. 40° C. The mixture was stirred for 4 hours after the addition and the bulk of the DMF evaporated under vacuum. The residue was treated with water (200 ml) and the crystalline precipitate collected, washed with water and dried. Yield 24.75 g (77%). m.p. 118°-119° C.

Workup

  1. customrose to ca. 40° C
  2. additionafter the addition
  3. customthe bulk of the DMF evaporated under vacuum
  4. additionThe residue was treated with water (200 ml)
  5. customthe crystalline precipitate collected
  6. washwashed with water
  7. customdried

Sources & evidence

ORD record
ord-828ce91b0e3e49e1a6c32f8a69bce7e0
Source dataset
uspto-grants-1978_10
Patent number
US04123529

Reaction notes

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