Water → HCID 14552619, compound

HRID 1073419Notes

Reaction equation

HRID 1073419 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-(1methylpropylthio)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-c0ecdecf1aeb4822957140226db9ccca
Source dataset
uspto-grants-1990_11
Patent number
US04968829

Reaction notes

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