Water → N-(1-Chlorobutan-2-yl)acetamide

HRID 267847Notes

Reaction equation

HRID 267847 reaction equation
[C:1](#[N:3])[CH3:2].[OH2:4].C([O-])([O-])=O.[Na+].[Na+].[CH2:11]=[CH:12][CH2:13][CH3:14].[Cl:15]Cl>>[Cl:15][CH2:11][CH:12]([NH:3][C:1](=[O:4])[CH3:2])[CH2:13][CH3:14]

Participants

6

Reactant 5

HCID 962WaterHCID 6342AcetonitrileHCID 78441-ButeneHCID 10340Sodium CarbonateHCID 24526Chlorine

Product 1

HCID 12803237N-(1-Chlorobutan-2-yl)acetamideYield 44%

Conditions

Temperature
25 °C

Procedure

A 500 ml. 3-necked flask fitted with a stirrer and dry ice-acetone trap is charged with 82.1 g. (2.0 mole) acetonitrile, 27.4 g. (1.52 mole) water, 27 g. (0.25 mole) Na2CO3 and 28.1 g. (0.50 mole) 1-butene and cooled to 0° C. Chlorine (0.50 mole) is added over one-half hour, the reaction temperature reaching a high of 32° C. After stirring for 2 hours at 25° C., the reaction mixture is filtered. The acetonitrile washings of the solid phase and filtrate is combined and the solvents removed by vacuum distillation to leave 33.0 g. of the N-[1-(chloromethyl)propyl]acetamide (44.0% yield based on 1-butene).

Workup

  1. custom3-necked flask fitted with a stirrer and dry ice-acetone trap
  2. additionis charged with 82.1 g
  3. customhigh of 32° C
  4. filtrationthe reaction mixture is filtered
  5. customthe solvents removed by vacuum distillation
  6. customto leave 33.0 g

Sources & evidence

ORD record
ord-3f1118d15bc0464a82a85e36e3d005e9
Source dataset
uspto-grants-1976_03
Patent number
US03944619

Reaction notes

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