Water → HCID 14552635, compound

HRID 2248180Notes

Reaction equation

HRID 2248180 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-2c6b5f10a86f495286d34cc26602064a
Source dataset
uspto-grants-1991_08
Patent number
US05037991

Reaction notes

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