2,2'-Bipyridine → Carbamic acid, (2-ethoxyphenyl)-, ethyl ester (9CI)

HRID 1084984Notes

Reaction equation

HRID 1084984 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH:8][C:9]([O:11][CH2:12][CH3:13])=[O:10].[O-:14][CH2:15][CH3:16].[Na+].N1C=CC=CC=1C1C=CC=CN=1.C(OCC)(=O)C>CO>[CH2:15]([O:14][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH:8][C:9]([O:11][CH2:12][CH3:13])=[O:10])[CH3:16]

Participants

6

Reactant 4

HCID 14742,2'-BipyridineHCID 8857Ethyl AcetateHCID 2723922Sodium ethoxideHCID 4182114Carbamic acid, (2-bromophenyl)-, ethyl ester

Product 1

HCID 307457Carbamic acid, (2-ethoxyphenyl)-, ethyl ester (9CI)Yield 84%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

2.44 g of the 2-bromo-1-ethoxycarbonylaminobenzene was added to a solution containing 680 mg of sodium ethoxide, 170 mg of cupric chloride dihydrate, and 156 mg of 2,2'-bipyridine in 40 ml of methanol, and the mixture was heated under reflux for 1.5 hours. After the temperature was brought to room temperature, ethyl acetate was added thereto, and the resulting mixture was washed with water and dried over Glauber's salt. The solvent was distilled off, and the obtained crude crystals were recrystallized from a n-hexane/ethyl acetate solvent mixture, to obtain 1.75 g (yield: 84%) of the desired compound. The spectrum data of the compound was in agreement with the spectrum data of the separately synthesized reference compound.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 1.5 hours
  3. customwas brought to room temperature
  4. washthe resulting mixture was washed with water
  5. dry with materialdried over Glauber's salt
  6. distillationThe solvent was distilled off
  7. customthe obtained crude crystals
  8. customwere recrystallized from a n-hexane/ethyl acetate solvent mixture

Sources & evidence

ORD record
ord-1e988eddc57242e286eaddb6360593da
Source dataset
uspto-grants-1991_04
Patent number
US05006660

Reaction notes

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