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

HRID 1891346Notes

Reaction equation

HRID 1891346 reaction equation
[CH3:1][C:2]([CH3:7])=[CH:3][C:4](Cl)=[O:5].[NH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.C(N(C(C)C)CC)(C)C.C(=O)(O)[O-].[Na+]>C(Cl)Cl>[C:9]1([NH:8][C:4](=[O:5])[CH:3]=[C:2]([CH3:7])[CH3:1])[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

6

Reactant 4

HCID 6115AnilineHCID 81531DiisopropylethylamineHCID 1023943-Methyl-2-butenoyl chlorideHCID 516892Sodium Bicarbonate

Product 1

HCID 123870223-Methyl-N-phenylbut-2-enamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To 3,3-dimethylacryloyl chloride (4.8 mL, 43.2 mmol) in dry DCM (100 mL), was added aniline (4.02 g, 43.2 mmol) followed by diisopropylethylamine (14.28 mL, 86.4 mmol). The mixture was stirred at ambient temperature for 2 hrs. Saturated sodium bicarbonate was added to quench the reaction. The organic layer was separated and washed with sat NaHCO3 (50 mL) and water (50 mL×2). The resulting solution was dried over MgSO4 and the filtrate evaporated to afford 3-methyl-but-2-enoic acid phenylamide as a brown solid in quantitative yield (7.6 g). MS: 176.0 (M+H)+; tR=2.40 min (method 1).

Workup

  1. customto quench
  2. customthe reaction
  3. customThe organic layer was separated
  4. washwashed with sat NaHCO3 (50 mL) and water (50 mL×2)
  5. dry with materialThe resulting solution was dried over MgSO4
  6. customthe filtrate evaporated

Sources & evidence

ORD record
ord-0f79540178d34d2cbc9ade7a67b52fab
Source dataset
uspto-grants-2013_08
Patent number
US08507536B2

Reaction notes

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