4-Chlorobenzoic Acid → 4-Chloro-3-dichloroacetylaminomethylbenzoic acid

HRID 376791Notes

Reaction equation

HRID 376791 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][CH:3]=1.O[CH2:12][NH:13][C:14](=[O:18])[CH:15]([Cl:17])[Cl:16]>S(=O)(=O)(O)O>[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][C:3]=1[CH2:12][NH:13][C:14](=[O:18])[CH:15]([Cl:17])[Cl:16]

Participants

4

Reactant 2

HCID 63184-Chlorobenzoic AcidHCID 12832764N-hydroxymethyl dichloroacetamide

Product 1

HCID 193592184-Chloro-3-dichloroacetylaminomethylbenzoic acidYield 89%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

The title compound was prepared by modification of procedures previously reported in the literature (Felder et al (1965) Helv. Chim. Acta, 48: 259). To a solution of 4-chlorobenzoic acid (15.7 g, 100 mmol) in 150 ml of concentrated sulfuric acid was added N-hydroxymethyl dichloroacetamide (23.7 g, 150 mmol) in portions. The reaction mixture was stirred at room temperature for 2 days, poured onto 375 g of ice, stirred for 1 hour, the solid was collected by filtration, and washed with H2O. The moist solid was dissolved in 5% sodium bicarbonate solution, filtered, and acidified to pH 1 with concentrated HCl. The solid was collected by filtration, washed with H2O, and air-dryed overnight to give 4-chloro-3-dichloroacetylaminomethylbenzoic acid (26.2 g, 89%) as a white powder.

Workup

  1. stirringstirred for 1 hour
  2. filtrationthe solid was collected by filtration
  3. washwashed with H2O
  4. dissolutionThe moist solid was dissolved in 5% sodium bicarbonate solution
  5. filtrationfiltered
  6. filtrationThe solid was collected by filtration
  7. washwashed with H2O, and air-dryed overnight

Sources & evidence

ORD record
ord-50cd5afa460e4c4c9ceea077ace89567
Source dataset
uspto-grants-2000_02
Patent number
US06022523

Reaction notes

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