Water → HCID 14552617, compound

HRID 2248169Notes

Reaction equation

HRID 2248169 reaction equation
[CH3:1][CH:2]([S:5][C:6]1[CH:15]=[CH:14][C:9]([O:10][CH2:11][CH2:12][OH:13])=[CH:8][CH:7]=1)[CH2:3][CH3:4].C(=O)([O-])[O-].[K+].[K+].[CH2:22]([N:24]=[C:25]=[S:26])[CH3:23].O>CN(C=O)C>[CH2:22]([NH:24][C:25](=[S:26])[O:13][CH2:12][CH2:11][O:10][C:9]1[CH:14]=[CH:15][C:6]([S:5][CH:2]([CH3:1])[CH2:3][CH3:4])=[CH:7][CH:8]=1)[CH3:23]

Participants

6

Reactant 4

HCID 962WaterHCID 10966Ethyl isothiocyanateHCID 11430Potassium CarbonateHCID 14852817HCID 14852817, compound

Product 1

HCID 14552617HCID 14552617, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A mixture of the above alcohol (2.16 g, 10.0 mmol) and potassium carbonate (1.66 g, 12.0 mmol) in 10 ml of DMF is cooled to 5° and ethyl isothiocyanate (1.10 ml, 12.0 mmol) in 10 ml of DMF is added dropwise. After addition is complete, the mixture is allowed to warm to RT and is stirred at RT overnight. Water is added and the aqueous phase is extracted with ether. The combined organic layers are washed with water and brine, dried, the solvent removed and the residue is purified by column chromatography to give O-2-[4-(1-methylpropylthio)phenoxy]ethyl N-ethylthiocarbamate (compound 38, Table A).

Workup

  1. temperatureis cooled to 5°
  2. additionAfter addition
  3. extractionthe aqueous phase is extracted with ether
  4. washThe combined organic layers are washed with water and brine
  5. customdried
  6. customthe solvent removed
  7. customthe residue is purified by column chromatography

Sources & evidence

ORD record
ord-5b536f42f96c4510863886874eb48c6a
Source dataset
uspto-grants-1991_08
Patent number
US05037991

Reaction notes

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