Sodium Hydroxide → HCID 12898695, compound

HRID 372026Notes

Reaction equation

HRID 372026 reaction equation
[OH-:1].[Na+].[CH2:3]([NH:7][C:8]1[CH:13]=[CH:12][C:11]([Cl:14])=[C:10]([C:15]([F:18])([F:17])[F:16])[CH:9]=1)[CH2:4][CH2:5][CH3:6]>>[CH2:3]([N:7]([C:3]1[O:1][C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=2[N:7]=1)[C:8]1[CH:13]=[CH:12][C:11]([Cl:14])=[C:10]([C:15]([F:18])([F:16])[F:17])[CH:9]=1)[CH2:4][CH2:5][CH3:6]

Participants

3

Reactant 2

HCID 14798Sodium HydroxideHCID 23455842HCID 23455842, compound

Product 1

HCID 12898695HCID 12898695, compound

Procedure

Hydrolysis of this N-(n-butyl)benzanilide (33 g., 0.093 mole) was accomplished by adding it to a solution of sodium hydroxide (10.8 g., 0.372 mole) in 200 ml. of water and 100 ml. of ethanol. The resulting solution was heated under reflux for 20 hours. The ethanol was then removed by distillation under vacuum. The remaining basic solution was extracted with diethyl ether; the ether extract was dried over magnesium sulfate and filtered. The filtrate was evaporated to dryness by distillation under vacuum. The crude product obtained was purified by addition of 6 N hydrochloric acid and separation of the water-insoluble salts thus formed. The acidic solution was then made basic by the addition of an aqueous 10% sodium hydroxide solution. The product was again extracted with ether and dried, as described above, to give 16.9 g. of N-(n-butyl)-4-chloro-3-(trifluoromethyl)aniline.

Workup

  1. customwas purified by addition of 6 N hydrochloric acid and separation of the water-insoluble salts
  2. customthus formed
  3. extractionThe product was again extracted with ether
  4. customdried
  5. customto give 16.9 g

Sources & evidence

ORD record
ord-b914df9e2bab41a28d93278521ee1cb3
Source dataset
uspto-grants-1978_05
Patent number
US04088770

Reaction notes

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