Ammonia → 3-Ethenylbenzamide

HRID 660479Notes

Reaction equation

HRID 660479 reaction equation
[CH:1]([C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][CH:11]=1)[C:6](Cl)=[O:7])=[CH2:2].[NH3:12]>CCOC(C)=O>[CH:1]([C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][CH:11]=1)[C:6]([NH2:12])=[O:7])=[CH2:2]

Participants

4

Reactant 2

HCID 222AmmoniaHCID 125414943-Vinylbenzoyl chloride

Product 1

HCID 125414983-Ethenylbenzamide

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

3-Vinylbenzoyl chloride is saturated with ammonia gas to afford an immediate precipitate. This mixture is poured into EtOAc and extracted with water and brine. The EtOAc is dried, filtered, and concentrated to afford the title compound: mp=128-130° C.; 1H NMR (CDCl3) δ 7.86 (d, J=1.3 Hz, 1H), 7.66 (dd, J=8.6, 1.0 Hz, 1H), 7.57 (d, 7.8 Hz, 1H), 7.41 (t, 7.8 Hz, 1H), 6.75 (dd, J=17.4, 10.9 Hz, 1H), 6.05 (br s, 1H), 5.83 (d, J=17.9 Hz, 1H), 5.61 (br s, 1H), 5.34 (d, J=10.9 Hz, 1H).

Workup

  1. customto afford an immediate precipitate
  2. extractionextracted with water and brine
  3. dry with materialThe EtOAc is dried
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-5c3b0affa6304507b61757bb6b1df008
Source dataset
uspto-grants-2011_12
Patent number
US08084448B2

Reaction notes

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