Acetic Acid → 4-(Diethylamino)-3-(trifluoromethyl)benzoic acid

HRID 1441734Notes

Reaction equation

HRID 1441734 reaction equation
[CH2:1]([N:3]([CH2:16][CH3:17])[C:4]1[CH:11]=[CH:10]C(C#N)=[CH:6][C:5]=1[C:12]([F:15])([F:14])[F:13])[CH3:2].Cl.[C:19]([OH:22])(=[O:21])[CH3:20]>>[CH2:16]([N:3]([CH2:1][CH3:2])[C:4]1[CH:11]=[CH:10][C:20]([C:19]([OH:22])=[O:21])=[CH:6][C:5]=1[C:12]([F:13])([F:14])[F:15])[CH3:17]

Participants

4

Reactant 3

HCID 176Acetic AcidHCID 313Hydrochloric AcidHCID 686774484-(Diethylamino)-3-(trifluoromethyl)benzonitrile

Product 1

HCID 114926394-(Diethylamino)-3-(trifluoromethyl)benzoic acid

Conditions

Temperature
95 °C

Procedure

A mixture of 4-diethylamino-3-(trifluoromethyl)-benzonitrile (1.21 g, 5 mmol), 12 mL of acetic acid and 8 mL of fuming hydrochloric acid (37%) is shaken for 20 hours at 95° C. After cooling, the reaction mixture is evaporated to dryness under reduced pressure. The solid residue is dissolved in a warm half-saturated aqueous sodium carbonate solution and the pH is adjusted to ˜5-6 by dropwise addition of 2M hydrochloric acid. The formed precipitate is filtered off, washed with water and dried in vacuo to yield a white solid.

Workup

  1. temperatureAfter cooling
  2. customthe reaction mixture is evaporated to dryness under reduced pressure
  3. dissolutionThe solid residue is dissolved in a warm half-saturated aqueous sodium carbonate solution
  4. additionthe pH is adjusted to ˜5-6 by dropwise addition of 2M hydrochloric acid
  5. filtrationThe formed precipitate is filtered off
  6. washwashed with water
  7. customdried in vacuo
  8. customto yield a white solid

Sources & evidence

ORD record
ord-fc044b554a0b405d820030a58fe4328e
Source dataset
uspto-grants-2010_02
Patent number
US07655669B2

Reaction notes

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