Benzene → 3-Methyl-N-phenylbutanimidic acid

HRID 2292266Notes

Reaction equation

HRID 2292266 reaction equation
C(O[C:5](=[O:7])[CH3:6])(=O)C.C([C:11]1[CH:17]=[CH:16][CH:15]=[CH:14][C:12]=1[NH2:13])(C)C.[CH:18]1[CH:23]=CC=C[CH:19]=1>>[CH:18]([CH2:6][C:5]([NH:13][C:12]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:11]=1)=[O:7])([CH3:23])[CH3:19]

Participants

4

Reactant 3

HCID 241BenzeneHCID 7918Acetic Anhydride2×HCID 125612-Isopropylaniline

Product 1

HCID 2229413-Methyl-N-phenylbutanimidic acid

Conditions

Temperature
20 °C

Procedure

86 g of acetic acid anhydride were added to a solution of 108 g of 2-isopropyl-aniline and 250 ml of benzene and another 86 g of acetic acid anhydride were added thereto. The mixture was stirred at 20° C. for 16 hours and was washed with water, with aqueous sodium bicarbonate, with water, dried and evaporated to dryness under reduced pressure. The residue was triturated with hexane, cooled and filtered. The product was washed with hexane and dried under reduced pressure to obtain 115 g of 2-isopropylacetanilide melting at 67°-68° C.

Workup

  1. washwas washed with water, with aqueous sodium bicarbonate, with water
  2. customdried
  3. customevaporated to dryness under reduced pressure
  4. customThe residue was triturated with hexane
  5. temperaturecooled
  6. filtrationfiltered
  7. washThe product was washed with hexane
  8. customdried under reduced pressure

Sources & evidence

ORD record
ord-99eed091c8534aa2810d9039a2908dd6
Source dataset
uspto-grants-1989_01
Patent number
US04801717

Reaction notes

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