Benzene → N,2-Diphenylacetamide

HRID 35903Notes

Reaction equation

HRID 35903 reaction equation
[C:1]1([CH2:7][C:8](Cl)=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C1C=CC=CC=1.[NH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>O>[C:1]1([CH2:7][C:8]([NH:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 241Benzene2×HCID 6115AnilineHCID 7679Phenylacetyl chloride

Product 1

HCID 225533N,2-DiphenylacetamideYield 65.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

A mixture of 5.84 g (37.81 mmol) phenylacetyl chloride and 50 mL benzene was stirred at 0° C. A solution of 3.52 g (2.0 equivs.) aniline and 50 mL benzene was added dropwise. After addition was complete, the mixture was allowed to warm to room temperature and stirred for 3 hrs. The mixture was poured into 100 mL water and was extracted with 3×100 mL ethyl acetate. The organic layers were combined and washed sequentially with 100 mL portions of 5% aqueous hydrochloric acid, water, saturated sodium carbonate and water. The organic layer was dried, filtered and solvent was removed from the filtrate to provide 5.24 g (24.80 mmol, 65%) phenylacetanilide as a tan solid, mp=114°-116° C. NMR (CDCl3 /TMS): 3.73 (s, 2H), 7.08 (t, 1H), 7.18 (bs, 1H), 7.25-7.43 (m, 9H). Mass spectrum

Workup

  1. additionAfter addition
  2. temperatureto warm to room temperature
  3. stirringstirred for 3 hrs
  4. extractionwas extracted with 3×100 mL ethyl acetate
  5. washwashed sequentially with 100 mL portions of 5% aqueous hydrochloric acid, water, saturated sodium carbonate and water
  6. customThe organic layer was dried
  7. filtrationfiltered
  8. customsolvent was removed from the filtrate

Sources & evidence

ORD record
ord-87caf37906ad43938199f7afe230bf02
Source dataset
uspto-grants-1995_05
Patent number
US05411977

Reaction notes

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