2,6-Dimethylaniline → HCID 7719612, compound

HRID 2165120Notes

Reaction equation

HRID 2165120 reaction equation
[F:1][C:2]([F:13])([F:12])[C:3]1[CH:11]=[CH:10][C:6]([C:7](Cl)=[O:8])=[CH:5][CH:4]=1.[CH3:14][C:15]1[CH:21]=[CH:20][CH:19]=[C:18]([CH3:22])[C:16]=1[NH2:17].C(N(CC)CC)C>O1CCCC1>[CH3:14][C:15]1[CH:21]=[CH:20][CH:19]=[C:18]([CH3:22])[C:16]=1[NH:17][C:7](=[O:8])[C:6]1[CH:10]=[CH:11][C:3]([C:2]([F:13])([F:12])[F:1])=[CH:4][CH:5]=1

Participants

5

Reactant 3

HCID 68962,6-DimethylanilineHCID 8471TriethylamineHCID 676074-(Trifluoromethyl)benzoyl chloride

Product 1

HCID 7719612HCID 7719612, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 25 g of 4-trifluoromethylbenzoyl chloride in tetrahydrofuran was added to 14.5 g of 2,6-dimethylaniline and 16.7 ml of triethylamine in tetrahydrofuran. The reaction was stirred at ambient temperature overnight, chilled, and filtered. The filtrate was evaporated in vacuo and the residue therefrom was dissolved in chloroform, washed sequentially with 1M hydrochloric acid, 1M sodium hydroxide, water, and a saturated sodium chloride solution, dried over sodium sulfate, filtered, and evaporated in vacuo. Crystallization from methanol provided the desired title product in 85% yield, m.p. 206°-207° C.

Workup

  1. temperaturechilled
  2. filtrationfiltered
  3. customThe filtrate was evaporated in vacuo
  4. dissolutionthe residue therefrom was dissolved in chloroform
  5. washwashed sequentially with 1M hydrochloric acid, 1M sodium hydroxide, water
  6. dry with materiala saturated sodium chloride solution, dried over sodium sulfate
  7. filtrationfiltered
  8. customevaporated in vacuo
  9. customCrystallization from methanol

Sources & evidence

ORD record
ord-c9accd0dd3184c0084c826e6317f83f5
Source dataset
uspto-grants-1990_07
Patent number
US04939163

Reaction notes

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