Hydrochloric Acid → N1-(2,4-Difluorobenzyl)-3-Chloro-2,2-Dimethylpropanamide

HRID 974399Notes

Reaction equation

HRID 974399 reaction equation
[F:1][C:2]1[CH:9]=[C:8]([F:10])[CH:7]=[CH:6][C:3]=1[CH2:4][NH2:5].N1C=CC=CC=1.[Cl:17][CH2:18][C:19]([CH3:24])([CH3:23])[C:20](Cl)=[O:21].Cl>C1(C)C=CC=CC=1>[Cl:17][CH2:18][C:19]([CH3:24])([CH3:23])[C:20]([NH:5][CH2:4][C:3]1[CH:6]=[CH:7][C:8]([F:10])=[CH:9][C:2]=1[F:1])=[O:21]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 613453-Chloro-2,2-dimethylpropanoyl chlorideHCID 27332442,4-Difluorobenzylamine

Product 1

HCID 2779689N1-(2,4-Difluorobenzyl)-3-Chloro-2,2-Dimethylpropanamide

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

28.6 g (0.20 mol) of 2,4-difluorobenzylamine and 19.0 g (0.24 mol) of pyridine are dissolved in 100 ml of toluene. 34.1 g (0.22 mol) of chloropivaloyl chloride are added dropwise to this solution at 20°-25° C. over the course of 15 minutes with ice-bath cooling. A suspension forms and is stirred for a further 3 hours at room temperature until the reaction is complete (GC check). For work-up, the pH is adjusted to between 1 and 2 using 50 ml of 2N hydrochloric acid. The white emulsion produced is extracted three times with 100 ml of toluene. The extract is washed with 100 ml of water, dried using magnesium sulfate and evaporated on a vacuum rotary evaporator. 49.2 g (94% of theory) of a yellow oil are obtained.

Workup

  1. temperaturecooling
  2. customThe white emulsion produced
  3. extractionis extracted three times with 100 ml of toluene
  4. washThe extract is washed with 100 ml of water
  5. customdried
  6. customevaporated on a vacuum rotary evaporator
  7. custom49.2 g (94% of theory) of a yellow oil are obtained

Sources & evidence

ORD record
ord-fc63af1e980343348e0addb8c65b36a5
Source dataset
uspto-grants-1991_11
Patent number
US05068371

Reaction notes

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