Triethylamine → 1-(4-Bromobenzoylamino)-2-(2-methylphenyl)ethane

HRID 1156867Notes

Reaction equation

HRID 1156867 reaction equation
[Br:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=O)=[CH:4][CH:3]=1.C(N(CC)CC)C.ClC(OCC)=O.[NH2:24][CH2:25][CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=1[CH3:33]>CN(C)C=O>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C:6]([NH:24][CH2:25][CH2:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=2[CH3:33])=[O:8])=[CH:9][CH:10]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 114644-Bromobenzoic acidHCID 20638682-Methylphenethylamine

Product 1

HCID 128518091-(4-Bromobenzoylamino)-2-(2-methylphenyl)ethane

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Forty (40) grams of 4-bromobenzoic acid was dissolved in 200 ml of dry dimethylformamide. While the solution was cooled with ice with stirring, 23 g of triethylamine and 22 g of ethyl chloroformate were added. After a lapse of 30 minutes, 28 g of 1-amino-2-(2-methylphenyl)ethane was added dropwise. The mixture was stirred at room temperature for 1 hour and then at 50° to 60° C. for 1 hour, and poured into ice water. The crystals precipitated were washed in water, dried, and recrystallized from cyclohexane to afford 49 g of 1-(4-bromobenzoylamino)-2-(2-methylphenyl)ethane as colorless needles having a melting point of 101.5° to 103.0° C.

Workup

  1. temperatureWhile the solution was cooled with ice
  2. stirringThe mixture was stirred at room temperature for 1 hour
  3. customThe crystals precipitated
  4. washwere washed in water
  5. customdried
  6. customrecrystallized from cyclohexane

Sources & evidence

ORD record
ord-4bdafa673d21438bb3a2b8e5496ab52e
Source dataset
uspto-grants-1982_06
Patent number
US04337256

Reaction notes

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