Ammonia → Benzeneacetamide, 4-chloro-alpha-(4-chlorophenyl)-

HRID 2265177Notes

Reaction equation

HRID 2265177 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:12]2[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][CH:13]=2)[C:9](O)=[O:10])=[CH:4][CH:3]=1.[NH3:19]>O=S(Cl)Cl>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:12]2[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][CH:13]=2)[C:9]([NH2:19])=[O:10])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 222AmmoniaHCID 6730Bis(4-chlorophenyl)acetic acid

Product 1

HCID 182699Benzeneacetamide, 4-chloro-alpha-(4-chlorophenyl)-Yield 100%

Reagents, catalysts & solvents 1

HCID 24386Thionyl ChlorideSolvent

Procedure

A suspension of 2,2-bis-(4-chloro-phenyl)-acetic acid (0.50 g, 1.8 mmol) in SOCl2 (5 mL) was heated at reflux for 1 h. The mixture was concentrated, and the residue was azeotroped with toluene (3×). The crude acid chloride was stirred in DCM (10 mL) at rt and treated with NH3 (0.5 M in dioxane, 14 mL, 7.5 mmol). After 1 h, the reaction mixture was concentrated, and the residue was diluted with satd. aq. NaHCO3 and extracted with DCM (3×). The combined organics were dried (Na2SO4) and concentrated to provide the amide as a white solid (0.50 g, 100%). The amide was used without further purification. 1H NMR (400 MHz, CDCl3): 7.35-7.28 (m, 4H), 7.23-7.17 (m, 4H), 5.69 (br s, 1H), 5.53 (br s, 1H), 4.87 (s, 1H).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 1 h
  3. concentrationThe mixture was concentrated
  4. customthe residue was azeotroped with toluene (3×)
  5. concentrationthe reaction mixture was concentrated
  6. additionthe residue was diluted with satd
  7. extractionaq. NaHCO3 and extracted with DCM (3×)
  8. dry with materialThe combined organics were dried (Na2SO4)
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-a92a575f616240cb815b22f66adb5860
Source dataset
uspto-grants-2010_12
Patent number
US07855292B2

Reaction notes

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