Acetic Acid → 2-chloro-N-(4-methoxybenzyl)acetamide

HRID 434590Notes

Reaction equation

HRID 434590 reaction equation
C(O)(=O)C.S(=O)(=O)(O)O.[C:10]1([O:16][CH3:17])[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.O[CH2:19][NH:20][C:21](=[O:24])[CH2:22][Cl:23]>O>[CH3:17][O:16][C:10]1[CH:15]=[CH:14][C:13]([CH2:19][NH:20][C:21](=[O:24])[CH2:22][Cl:23])=[CH:12][CH:11]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 1118Sulfuric AcidHCID 7519AnisoleHCID 62466N-Methylol-alpha-chloroacetamide

Product 1

HCID 24048332-chloro-N-(4-methoxybenzyl)acetamideYield 41%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Into an ice-cooled mixture of 80 ml of acetic acid and 20 ml of 95% sulfuric acid, 16 g of anisol and 12.4 g of N-hydroxymethyl-2-chloroacetamide (refer to Beilsteins, Handbuch der Organischen Chemie, Vol. 2, 200) were added under agitation, and after stirring the reaction mixture for 30 min, it was left stand still for 2 days. Then, the reaction mixture was poured into iced water and the thus deposited white crystals were collected by filtration. The crystals were recrystallized from an aqueous ethyl alcoholic solution to obtain 8.7 g of the object product in a yield of 41%. The product melted at 101°-102° C., and showed infrared absorption peaks at 3320 cm-1 (due to NH), 1640 cm-1 (due to C=O) and 1260 cm-1 (due to --O--), respectively.

Workup

  1. additionwere added under agitation
  2. waitit was left stand still for 2 days
  3. filtrationthe thus deposited white crystals were collected by filtration
  4. customThe crystals were recrystallized from an aqueous ethyl alcoholic solution

Sources & evidence

ORD record
ord-98275c1499d54e34af612107d3ead349
Source dataset
uspto-grants-1983_08
Patent number
US04398944

Reaction notes

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