Carbon Disulfide → 4-(Tetrahydrofuran-2-ylmethylthiocarbamoylsulfanyl)-butyric acid methyl ester

HRID 352571

Reaction equation

HRID 352571 reaction equation
[CH2:1]([NH2:7])[CH:2]1[O:6][CH2:5][CH2:4][CH2:3]1.[OH-].[Na+].[C:10](=[S:12])=[S:11].Cl[CH2:14][CH2:15][CH2:16][C:17]([O:19][CH3:20])=[O:18]>CCO>[CH3:20][O:19][C:17](=[O:18])[CH2:16][CH2:15][CH2:14][S:11][C:10](=[S:12])[NH:7][CH2:1][CH:2]1[CH2:3][CH2:4][CH2:5][O:6]1

Participants

6

Reactant 4

HCID 6348Carbon DisulfideHCID 14798Sodium HydroxideHCID 76612Butanoic acid, 4-chloro-, methyl esterHCID 253298Tetrahydrofurfurylamine

Product 1

HCID 99037334-(Tetrahydrofuran-2-ylmethylthiocarbamoylsulfanyl)-butyric acid methyl ester

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of tetrahydofurfurylamine (2 mL) in EtOH (20 mL) were added 5 N NaOH (3.9 mL) and carbon disulfide (1.17 mL), and the mixture was stirred for 1.5 h. Methyl 4-chlorobutyrate (2.4 mL) was then added, and the mixture was stirred overnight. Upon quenching with saturated NaCl solution the mixture was extracted with ether. Chromatography on silica gel gave the desired 4-(tetrahydrofuran-2-ylmethylthiocarbamoylsulfanyl)-butyric acid methyl ester product (1.1 g).

Workup

  1. stirringthe mixture was stirred overnight
  2. customUpon quenching with saturated NaCl solution the mixture
  3. extractionwas extracted with ether

Sources & evidence

ORD record
ord-4bd9eb844c2a4b3f994ea8ed6e3ff0e7
Source dataset
uspto-grants-2004_06
Patent number
US06747061B2

Linked notes

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