Water → HCID 14552619, compound

HRID 2248173Notes

Reaction equation

HRID 2248173 reaction equation
[CH3:1][CH:2]([S:5][C:6]1[CH:15]=[CH:14][C:9]([O:10][CH2:11][CH2:12][NH2:13])=[CH:8][CH:7]=1)[CH2:3][CH3:4].C(=O)([O-])[O-].[K+].[K+].Cl[C:23]([O:25][CH2:26][CH3:27])=[O:24].O>CN(C=O)C>[CH3:1][CH:2]([S:5][C:6]1[CH:15]=[CH:14][C:9]([O:10][CH2:11][CH2:12][NH:13][C:23](=[O:24])[O:25][CH2:26][CH3:27])=[CH:8][CH:7]=1)[CH2:3][CH3:4]

Participants

6

Reactant 4

HCID 962WaterHCID 10928Ethyl chloroformateHCID 11430Potassium CarbonateHCID 15662551HCID 15662551, compound

Product 1

HCID 14552619HCID 14552619, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a solution of the above amine (2.41 g, 10.0 mmol) in 10 ml DMF, cooled to 0° and under N2, is added potassium carbonate (1.66 g, 12.0 mmol) followed by dropwise addition of ethyl chloroformate (1.2 ml, 12.0 mmol) in 5 ml of DMF. After 1.5 hours, water is added and the aqueous phase is extracted with ether. The combined organic layers are washed with water and brine, dried, rotoevaporated and the residue is purified by column chromatography to give ethyl N-{2-[4-(1-methylpropylthio)phenoxy]ethyl}carbamate (compound 40, Table A).

Workup

  1. extractionthe aqueous phase is extracted with ether
  2. washThe combined organic layers are washed with water and brine
  3. customdried
  4. customthe residue is purified by column chromatography

Sources & evidence

ORD record
ord-a485e71bc0fb411385d8105ddf166100
Source dataset
uspto-grants-1991_08
Patent number
US05037991

Reaction notes

Loading…