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Potassium Carbonate → HCID 20329833, compound

HRID 2058074
Notes
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Reaction equation

HRID 2058074 reaction equation
[Cl:1][C:2]1[CH:18]=[CH:17][C:5]([NH:6][CH2:7][C:8]2[CH:13]=[CH:12][C:11]([OH:14])=[C:10]([O:15][CH3:16])[CH:9]=2)=[CH:4][CH:3]=1.Br[C:20]([CH3:27])([CH3:26])[C:21]([O:23][CH2:24][CH3:25])=[O:22].C(=O)([O-])[O-].[K+].[K+]>C(C(C)=O)C(C)C>[Cl:1][C:2]1[CH:18]=[CH:17][C:5]([NH:6][CH2:7][C:8]2[CH:13]=[CH:12][C:11]([O:14][C:20]([CH3:27])([CH3:26])[C:21]([O:23][CH2:24][CH3:25])=[O:22])=[C:10]([O:15][CH3:16])[CH:9]=2)=[CH:4][CH:3]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 11745Propanoic acid, 2-bromo-2-methyl-, ethyl ester2×HCID 122734974-{[(4-Chlorophenyl)amino]methyl}-2-methoxyphenol

Product 1

HCID 20329833HCID 20329833, compoundYield 40.4%

Reagents, catalysts & solvents 1

HCID 7909Methyl Isobutyl KetoneSolvent

Procedure

A mixture of 1.9 g of 4-(4-chloroanilinomethyl)-2-methoxyphenol, 2.11 g of ethyl 2-bromo-2-methylpropionate 1.5 g of potassium carbonate and 29 ml of methyl isobutyl ketone is refluxed for 24 hours. To the mixture is further added 705 mg of ethyl 2-bromo-2-methylpropionate and the resulting mixture is further refluxed for 3 hours. The insolubles are filtered off and the filtrate is washed with water, dried and concentrated under reduced pressure. The residual oil is purified by column chromatography, using 60 g of silica gel and benzene as a developer, to give 1.1 g of ethyl 2-[4-(4-chloroanilinomethyl)-2-methoxyphenoxy]-2-methylpropionate, mp 73° to 74° C. Infrared absorption spectrum (nujol) 3400, 1735 cm-1. N.M.R.spectrum (CDCl3, δ) ppm 6.45-7.33 (7H, m), 4.25 (2H, q, J=7 Hz), 4.20 (2H, s) 3.79 (3H, s), 1.59 (6H, s), 1.30 (3H, t, J=7 Hz)

Workup

  1. temperatureis refluxed for 24 hours
  2. temperaturethe resulting mixture is further refluxed for 3 hours
  3. filtrationThe insolubles are filtered off
  4. washthe filtrate is washed with water
  5. customdried
  6. concentrationconcentrated under reduced pressure
  7. customThe residual oil is purified by column chromatography

Sources & evidence

ORD record
ord-3a1b2feb04dc49758fa6de6f9d733de1
Source dataset
uspto-grants-1980_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04214094

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes