Triethylamine → HCID 22708276, compound

HRID 353192Notes

Reaction equation

HRID 353192 reaction equation
[C:1]([C:5]1[CH:11]=[CH:10][C:8]([NH2:9])=[C:7]([CH3:12])[CH:6]=1)([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.[Br:20][CH2:21][C:22](Br)=[O:23].C(OCC)(=O)C>ClCCl>[Br:20][CH2:21][C:22]([NH:9][C:8]1[CH:10]=[CH:11][C:5]([C:1]([CH3:4])([CH3:3])[CH3:2])=[CH:6][C:7]=1[CH3:12])=[O:23]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 61147Bromoacetyl bromideHCID 762004-tert-Butyl-o-toluidine

Product 1

HCID 22708276HCID 22708276, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

5.5 g (33.69 mmol) of 4-tert-butyl-2-methylaniline and 3.75 g (37.06 mmol) of triethylamine are initially charged in 150 ml of dichloromethane. At 0°-5° C., 7.48 g (37.06 mmol) of bromoacetyl bromide, dissolved in 90 ml of dichloromethane, are added dropwise, and a light-brown precipitate is formed. The mixture is stirred at room temperature overnight. 150 ml of ethyl acetate are then added to the reaction mixture, which is extracted successively with water, 1 N hydrochloric acid, water, saturated sodium bicarbonate soluton and water. The organic phase is dried over magnesium sulphate and freed from the solvent under reduced pressure. The residue is purified chromatographically. The product is recrystallized from ethyl acetate and n-pentane, filtered off with suction and dried under reduced pressure at 40° C. This gives 6.53 g (68% of theory) of the title compound.

Workup

  1. additionare added dropwise
  2. customa light-brown precipitate is formed
  3. extractionis extracted successively with water, 1 N hydrochloric acid, water, saturated sodium bicarbonate soluton and water
  4. dry with materialThe organic phase is dried over magnesium sulphate
  5. customThe residue is purified chromatographically
  6. customThe product is recrystallized from ethyl acetate and n-pentane
  7. filtrationfiltered off with suction
  8. customdried under reduced pressure at 40° C

Sources & evidence

ORD record
ord-259be7b6a1154a2c928e780562f27e78
Source dataset
uspto-grants-2004_06
Patent number
US06750236B2

Reaction notes

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