2,6-Dimethylaniline → HCID 7719612, compound

HRID 1762860Notes

Reaction equation

HRID 1762860 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-83968c31cc2c449e9414ac58aba05b1d
Source dataset
uspto-grants-1989_05
Patent number
US04835181

Reaction notes

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