Ethyl chloroformate → HCID 9517640, compound

HRID 1290790Notes

Reaction equation

HRID 1290790 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:7]=[C:8]([O:12][CH3:13])[C:9]=1[O:10][CH3:11])[NH2:6].C(=O)([O-])[O-].[K+].[K+].Cl[C:21]([O:23][CH2:24][CH3:25])=[O:22]>O1CCCC1>[CH3:13][O:12][C:8]1[CH:7]=[C:5]([NH:6][C:21](=[O:22])[O:23][CH2:24][CH3:25])[CH:4]=[C:3]([O:2][CH3:1])[C:9]=1[O:10][CH3:11]

Participants

5

Reactant 3

HCID 10928Ethyl chloroformateHCID 11430Potassium CarbonateHCID 322853,4,5-Trimethoxyaniline

Product 1

HCID 9517640HCID 9517640, compoundYield 72.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3,4,5-trimethoxyaniline (6 g) in tetrahydrofuran (125 ml) at room temperature was added potassium carbonate (5.42 g) followed by ethyl chloroformate (3.55 g). The mixture was stirred at room temperature for 48 hours, then solvent removed under reduced pressure. The residue was stirred with diethyl ether and filtered. The solid material remaining on the filter was extracted with acetone, the organic extracts combined, and solvent removed from the combined extracts under reduced pressure, to give a residue of ethyl 3,4,5-trimethoxyphenylcarbamate (6.05 g)

Workup

  1. customsolvent removed under reduced pressure
  2. stirringThe residue was stirred with diethyl ether
  3. filtrationfiltered
  4. extractionwas extracted with acetone
  5. customsolvent removed from the combined extracts under reduced pressure

Sources & evidence

ORD record
ord-062861e4f25549eaa3e2afea922120a1
Source dataset
uspto-grants-1998_05
Patent number
US05753663

Reaction notes

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