Water → methyl N-{2-[4-(1-methylpropoxy)phenoxy]ethyl}carbamate

HRID 2309844Notes

Reaction equation

HRID 2309844 reaction equation
[CH3:1][CH:2]([O:5][C:6]1[CH:11]=[CH:10][C:9]([OH:12])=[CH:8][CH:7]=1)[CH2:3][CH3:4].Cl[CH2:14][CH2:15][NH:16][C:17](=[O:20])[O:18][CH3:19].C(=O)([O-])[O-].[K+].[K+].O>CN(C)C=O>[CH3:1][CH:2]([O:5][C:6]1[CH:7]=[CH:8][C:9]([O:12][CH2:14][CH2:15][NH:16][C:17](=[O:20])[O:18][CH3:19])=[CH:10][CH:11]=1)[CH2:3][CH3:4]

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 251614Methyl (2-chloroethyl)carbamateHCID 138820044-(1-Methyl-1-propyloxy)-phenol

Product 1

HCID 15662569methyl N-{2-[4-(1-methylpropoxy)phenoxy]ethyl}carbamate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 4-(1-methylpropoxy)phenol (9.2 mmol), methyl 2-chloroethylcarbamate (11.9 mmol), and potassium carbonate (18.4 mmol) in 20 ml of dimethylformamide (DMF) is heated at 85° for 18 hours. The reaction mixture is cooled to room temperature (RT), poured into water and extracted with ether. The combined ether extracts are washed with water until neutral, followed with brine and dried over calcium sulfate. The solvent is removed in vacuo and the residue is placed under high vacuum at 80° for ca. 2 hours to remove the excess methyl 2-chloroethylcarbamate. Purification by preparative thin layer chromatography (prep. TLC) gives methyl N-{2-[4-(1-methylpropoxy)phenoxy]ethyl}carbamate.

Workup

  1. temperatureis heated at 85° for 18 hours
  2. extractionextracted with ether
  3. washThe combined ether extracts are washed with water until neutral,
  4. dry with materialdried over calcium sulfate
  5. customThe solvent is removed in vacuo
  6. customto remove the excess methyl 2-chloroethylcarbamate
  7. customPurification by preparative thin layer chromatography (prep. TLC)

Sources & evidence

ORD record
ord-add4aaf646714895ab7b855a5ef88067
Source dataset
uspto-grants-1987_09
Patent number
US04697033

Reaction notes

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