Triethylamine → HCID 22708283, compound

HRID 353191Notes

Reaction equation

HRID 353191 reaction equation
[CH:1]([C:4]1[CH:10]=[CH:9][C:7]([NH2:8])=[C:6]([C:11]([F:14])([F:13])[F:12])[CH:5]=1)([CH3:3])[CH3:2].C(N(CC)CC)C.[Br:22][CH2:23][C:24](Br)=[O:25]>ClCCl>[Br:22][CH2:23][C:24]([NH:8][C:7]1[CH:9]=[CH:10][C:4]([CH:1]([CH3:3])[CH3:2])=[CH:5][C:6]=1[C:11]([F:12])([F:13])[F:14])=[O:25]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 61147Bromoacetyl bromideHCID 27752232-amino-5-isopropylbenzotrifluoride

Product 1

HCID 22708283HCID 22708283, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

50 g (246.06 mmol) of 4-isopropyl-2-(trifluoromethyl)aniline and 27.39 g (270.66 mmol) of triethylamine are initially charged in 1000 ml of dichloromethane. At 0°-5° C., 54.63 g (270.66 mmol) of bromoacetyl bromide, dissolved in 200 ml of dichloromethane, are added dropwise. The mixture is stirred at room temperature for 20 hours. The reaction mixture is then extracted successively with water, 1 N hydrochloric acid, water, saturated sodium bicarbonate solution and water. The organic phase is dried over sodium sulphate and the solvent is removed under reduced pressure. The residue is purified chromatographically. The product is recrystallized from cyclohexane/n-pentane, filtered off with suction and dried under reduced pressure at 40° C. for 20 hours. This gives 32.45 g (41% of theory) of the title compound.

Workup

  1. additionare added dropwise
  2. extractionThe reaction mixture is then extracted successively with water, 1 N hydrochloric acid, water, saturated sodium bicarbonate solution and water
  3. dry with materialThe organic phase is dried over sodium sulphate
  4. customthe solvent is removed under reduced pressure
  5. customThe residue is purified chromatographically
  6. customThe product is recrystallized from cyclohexane/n-pentane
  7. filtrationfiltered off with suction
  8. customdried under reduced pressure at 40° C. for 20 hours

Sources & evidence

ORD record
ord-9b1885902ddf49559ec173f9162ec972
Source dataset
uspto-grants-2004_06
Patent number
US06750236B2

Reaction notes

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