Acetic Anhydride → N-[[4-(Tetradecyloxy)phenyl]methyl]acetamide

HRID 1728886Notes

Reaction equation

HRID 1728886 reaction equation
[CH2:1]([O:15][C:16]1[CH:21]=[CH:20][C:19]([CH2:22][NH2:23])=[CH:18][CH:17]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14].[C:24](OC(=O)C)(=[O:26])[CH3:25].C(=O)(O)[O-].[Na+]>C(Cl)Cl>[CH2:1]([O:15][C:16]1[CH:21]=[CH:20][C:19]([CH2:22][NH:23][C:24](=[O:26])[CH3:25])=[CH:18][CH:17]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14]

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 516892Sodium BicarbonateHCID 117234984-(Tetradecyloxy)benzenemethanamine

Product 1

HCID 19016453N-[[4-(Tetradecyloxy)phenyl]methyl]acetamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a room temperature mixture of 15 g of product from Example 99, 0.229 g of 4-N,N-dimethylaminopyridine and 50 ml of methylene chloride is added 5 ml of acetic anhydride. An additional 50 ml of methylene chloride is added and the solution is stirred at room temperature for 69 hours. The reaction is poured into half saturated sodium bicarbonate and extracted with methylene chloride. The combined organic layers are washed with half saturated sodium bicarbonate, water and saturated sodium chloride. The dried methylene chloride layer is concentrated in vacuo and purified by chromatography (silica gel: 5% methyl alcohol/chloroform) to give 16.29 g of the desired product as colorless prisms.

Workup

  1. extractionextracted with methylene chloride
  2. washThe combined organic layers are washed with half saturated sodium bicarbonate, water and saturated sodium chloride
  3. concentrationThe dried methylene chloride layer is concentrated in vacuo
  4. custompurified by chromatography (silica gel: 5% methyl alcohol/chloroform)

Sources & evidence

ORD record
ord-ecfe7556d2cf4a0baf413b373b75f073
Source dataset
uspto-grants-1994_07
Patent number
US05328921

Reaction notes

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