Chloroform → N-(2-bromoethyl)acetoacetamide

HRID 435957Notes

Reaction equation

HRID 435957 reaction equation
[CH2:1]=[C:2]1[O:6][C:4](=[O:5])[CH2:3]1.C(Cl)(Cl)Cl.Br.[Br:12][CH2:13][CH2:14][NH2:15].[OH-].[Na+]>O>[Br:12][CH2:13][CH2:14][NH:15][C:4](=[O:5])[CH2:3][C:2]([CH3:1])=[O:6]

Participants

6

Reactant 4

HCID 6212ChloroformHCID 12661DiketeneHCID 14798Sodium HydroxideHCID 27742172-Bromoethylamine hydrobromide

Product 1

HCID 21454933N-(2-bromoethyl)acetoacetamide

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

To a solution of 8.4 g. (0.1 mole) of diketene in 150 ml. of chloroform is added 21 g. (0.11 mole) of 2-bromoethylamine hydrobromide in 30 ml. of water, and the resulting mixture stirred vigorously at 0° C. while 4.1 g. (0.11 mole) of sodium hydroxide in 20 ml. of water is added dropwise over a period of 20 minutes. The reaction mixture is allowed to stir at room temperature for 1 hour, after which the chloroform layer is separated, dried over anhydrous sodium sulfate and concentrated to dryness in vacuo to yield the intermediate, N-(2-bromoethyl)acetoacetamide, as a white crystalline residue.

Workup

  1. customafter which the chloroform layer is separated
  2. dry with materialdried over anhydrous sodium sulfate
  3. concentrationconcentrated to dryness in vacuo

Sources & evidence

ORD record
ord-d36570aa19ac483fa519666f9a1161f5
Source dataset
uspto-grants-1977_02
Patent number
US04007184

Reaction notes

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