Potassium Carbonate → HCID 14552588, compound

HRID 1073397Notes

Reaction equation

HRID 1073397 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>[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

5

Reactant 3

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

Product 1

HCID 14552588HCID 14552588, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

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 chromatography (prep. TLC) gave ethyl N-{2-[4-(3-methyl-2-butenoxy)phenoxy]ethyl}carbamate (compound 1, Table A).

Workup

  1. temperatureheated 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 chromatography (prep. TLC)

Sources & evidence

ORD record
ord-1925154566e44ba79d43276ce33bae29
Source dataset
uspto-grants-1990_11
Patent number
US04968829

Reaction notes

Loading…