Triethylamine → HCID 66813756, compound

HRID 924573Notes

Reaction equation

HRID 924573 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[CH3:14].C(N(CC)CC)C.Cl[C:23]([O:25][CH2:26][CH3:27])=[O:24]>C1(C)C=CC=CC=1>[CH2:26]([O:25][C:23]([NH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[CH3:14])=[O:24])[CH3:27]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 12072412'-Methyl[biphenyl]-2-amine

Product 1

HCID 66813756HCID 66813756, compoundYield 46%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

The above compound, 2-amino-2′-methyl-biphenyl (11.0 g, 60 mmol) was added to dry toluene (250 mL) containing triethyl amine (24 g, 24 mmol) and stirred under a nitrogen pad. Ethyl chloroformate (26 g, 240 mmol) was slowly added to the stirred solution via a syringe. The reaction mixture was washed with brine and the organics separated, dried over magnesium sulfate and concentrated to give N-ethoxycarbonyl-2-amino-2′methyl biphenyl as a colorless oil (7.0 g, 46% yield) whose structure was confirmed by GCMS and NMR.

Workup

  1. washThe reaction mixture was washed with brine
  2. dry with materialthe organics separated, dried over magnesium sulfate
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-9867662007194222ad5dbbed2b759bf8
Source dataset
uspto-grants-2016_03
Patent number
US09281483B2

Reaction notes

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