Water → HCID 14552588, compound

HRID 2248151Notes

Reaction equation

HRID 2248151 reaction equation
[CH3:1][C:2]([CH3:13])=[CH:3][CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([OH:12])=[CH:8][CH:7]=1.Cl[CH2:15][CH2:16][NH:17][C:18](=[O:22])[O:19][CH2:20][CH3:21].C(=O)([O-])[O-].[K+].[K+].O>CN(C)C=O>[CH3:1][C:2]([CH3:13])=[CH:3][CH2:4][O:5][C:6]1[CH:7]=[CH:8][C:9]([O:12][CH2:15][CH2:16][NH:17][C:18](=[O:22])[O:19][CH2:20][CH3:21])=[CH:10][CH:11]=1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 80621Ethyl 2-chloroethylcarbamateHCID 11435274HCID 11435274, compound

Product 1

HCID 14552588HCID 14552588, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 4-(3-methyl-2-butenoxy)phenol (1.64 g, 9.2 mmol), ethyl 2-chloroethylcarbamate (1.81 g, 11.9 mmol), and potassium carbonate (2.54 g, 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 was removed in vacuo and the residue was placed under high vacuum at 80° for ca. 2 hours to remove the excess ethyl 2-chloroethylcarbamate. Purification by preparative thin layer chromotography (prep. TLC) gave ethyl N-{2-[4-(3-methyl-2-butenoxy)phenoxy]ethyl }-carbamate (compound 1, Table A).

Workup

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

Sources & evidence

ORD record
ord-7551af56b18d4887bf46e718d5fe5ec2
Source dataset
uspto-grants-1991_08
Patent number
US05037991

Reaction notes

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