Aniline → 2-Bromo-N-phenylacetamide

HRID 1599849Notes

Reaction equation

HRID 1599849 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Br:8][CH2:9][C:10](Br)=[O:11]>CN(C=O)C.O1CCOCC1>[Br:8][CH2:9][C:10]([NH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)=[O:11]

Participants

5

Reactant 2

HCID 6115AnilineHCID 61147Bromoacetyl bromide

Product 1

HCID 948182-Bromo-N-phenylacetamideYield 68%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 312751,4-DioxaneSolvent

Procedure

Aniline (19.4 g, 0.043 mol) was dissolved in the mixture of DMF (25 mL) and dioxane (25 mL). The solution was cooled to +5° C. and bromoacetyl bromide (3.8 mL=8.7 g, 100 mol %) was added dropwise over 30 min. The reaction mixture was warmed to room temperature and stirred for 7 h. The mixture was poured into ice-water, and the white crystalline compound which precipitated was filtered, washed several times with cold water, and then air dried for 24 h, giving 6.2 g (68%) of title compound: 1H NMR (CDCl3) δ8.20 (bs, 1H), 7.54 (dd, J=8.8, J=1.2, 2H), 7.37 (t, J=7.2, 1H), 7.18 (t, J=8, 1H), 4.03 (s, 2H): 13C NMR (CDCl3) δ163.35, 136.88, 129.21, 129.18, 129.11, 125.21, 120.03, 29.47; MS (El, m/z) 213 (M+).

Workup

  1. temperatureThe solution was cooled to +5° C.
  2. customthe white crystalline compound which precipitated
  3. filtrationwas filtered
  4. washwashed several times with cold water
  5. customair dried for 24 h

Sources & evidence

ORD record
ord-ec7570a491ae405ab73e4314bae0be09
Source dataset
uspto-grants-1998_04
Patent number
US05741926

Reaction notes

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