Sodium Carbonate → N-(1-Chlorobutan-2-yl)acetamide

HRID 267844Notes

Reaction equation

HRID 267844 reaction equation
[Cl:1][CH2:2][CH:3]([N:6]=[C:7](Cl)[CH3:8])[CH2:4][CH3:5].C(=O)([O-])[O-:11].[Na+].[Na+]>>[Cl:1][CH2:2][CH:3]([NH:6][C:7](=[O:11])[CH3:8])[CH2:4][CH3:5]

Participants

3

Reactant 2

HCID 10340Sodium CarbonateHCID 12803236(1E)-N-(1-Chlorobutan-2-yl)ethanimidoyl chloride

Product 1

HCID 12803237N-(1-Chlorobutan-2-yl)acetamide

Procedure

A sample of N-[1-(chloromethyl)propyl]acetimidoyl chloride from Example 8 is treated with an excess of 10% aqueous sodium carbonate solution at room temperature. The organic material is extracted with ether and dried over MgSO4. Removal of the solvent under reduced pressure leaves N-[1-(chloromethyl)propyl]acetamide as a crystalline solid in nearly quantitative yield. An infrared spectrum shows peaks at 3300(M), 3100(W), 1650(S), and 550(S) cm-1 ; nuclear magnetic resonance (CDCl3) shows peaks 0.95 ppm (t ,3H), 1.4-1.8 ppm (m ,2H), 2.03 ppm (s ,3H), 3.67 ppm (d,2H,CH2Cl), 3.8-4.4 ppm (m ,1H).

Workup

  1. extractionThe organic material is extracted with ether
  2. dry with materialdried over MgSO4
  3. customRemoval of the solvent under reduced pressure

Sources & evidence

ORD record
ord-d481624c4e444d16862e6a8db2302f43
Source dataset
uspto-grants-1976_03
Patent number
US03944617

Reaction notes

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