Aniline → 3-Methyl-N-phenylbut-2-enamide

HRID 74040Notes

Reaction equation

HRID 74040 reaction equation
[CH3:1][C:2]([CH3:7])=[CH:3][C:4](O)=[O:5].O=S(Cl)Cl.[NH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.CCN(CC)CC>>[C:13]1([NH:12][C:4](=[O:5])[CH:3]=[C:2]([CH3:7])[CH3:1])[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

5

Reactant 4

HCID 6115AnilineHCID 8471TriethylamineHCID 109313-Methyl-2-butenoic acidHCID 24386Thionyl Chloride

Product 1

HCID 123870223-Methyl-N-phenylbut-2-enamideYield 80%

Procedure

A mixture of 3-methyl-but-2-enoic acid (100 g, 1 mol) and SOCl2 (119 g, 1 mol) was heated at reflux for 3 h. The excess SOCl2 was removed under reduced pressure. CH2Cl2 (200 mL) was added followed by the addition of aniline (93 g, 1.0 mol) in Et3N (101 g, 1 mol) at 0° C. The mixture was stirred at room temperature for 1 h and quenched with HCl (5%, 150 mL). The aqueous layer was separated and extracted with CH2Cl2. The combined organic layers were washed with water (2×100 mL) and brine (100 mL), dried over Na2SO4 and concentrated to give 3-methyl-but-2-enoic acid phenylamide (120 g, 80%).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 3 h
  3. customThe excess SOCl2 was removed under reduced pressure
  4. additionCH2Cl2 (200 mL) was added
  5. customquenched with HCl (5%, 150 mL)
  6. customThe aqueous layer was separated
  7. extractionextracted with CH2Cl2
  8. washThe combined organic layers were washed with water (2×100 mL) and brine (100 mL)
  9. dry with materialdried over Na2SO4
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-945eeb3bc71c4ca99499aece47c9880e
Source dataset
uspto-grants-2014_09
Patent number
US08829204B2

Reaction notes

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