Water → HCID 14552635, compound

HRID 1073425Notes

Reaction equation

HRID 1073425 reaction equation
[CH3:1][CH:2]([O:5][C:6]1[CH:11]=[CH:10][C:9]([S:12][CH2:13][CH2:14][NH2:15])=[CH:8][CH:7]=1)[CH2:3][CH3:4].Cl[C:17]([O:19][CH2:20][CH3:21])=[O:18].[OH-].[Na+].O>CCOCC>[CH3:1][CH:2]([O:5][C:6]1[CH:7]=[CH:8][C:9]([S:12][CH2:13][CH2:14][NH:15][C:17](=[O:18])[O:19][CH2:20][CH3:21])=[CH:10][CH:11]=1)[CH2:3][CH3:4]

Participants

6

Reactant 4

HCID 962WaterHCID 10928Ethyl chloroformate2×HCID 14798Sodium HydroxideHCID 15662559HCID 15662559, compound

Product 1

HCID 14552635HCID 14552635, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

To a solution of 2-[4-(1-methylpropoxy)phenylthio]ethylamine (2.21 g, 8.65 mmol) in 25 ml of ether, at 0° and under N2, is added ethyl chloroformate (0.52 g, 4.76 mmol) by syringe, followed by addition of 10% aqueous sodium hydroxide (3.5 ml) and additional ethyl chloroformate (0.51 g, 4.76 mmol). After 15 min., the reaction is worked up by addition of water and extraction with ether. The combined organic phases are washed with 1N sulfuric acid, with water and with brine, dried and filtered, the filtrate is concentrated in vacuo and the product is purified by prep. TLC to give ethyl N-{2-[4-(1-methylpropoxy)phenylthio]ethyl}carbamate (compound 76, Table A).

Workup

  1. washThe combined organic phases are washed with 1N sulfuric acid, with water and with brine
  2. customdried
  3. filtrationfiltered
  4. concentrationthe filtrate is concentrated in vacuo
  5. customthe product is purified by prep

Sources & evidence

ORD record
ord-98d607146b034071b7028da05107a849
Source dataset
uspto-grants-1990_11
Patent number
US04968829

Reaction notes

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