2-Mercaptoethanol → HCID 54314561, compound

HRID 615740Notes

Reaction equation

HRID 615740 reaction equation
Cl[CH:2]([CH3:16])[C:3](=[O:15])[C:4](=[N:10][O:11][CH2:12][CH2:13][CH3:14])[C:5]([O:7][CH2:8][CH3:9])=[O:6].[SH:17][CH2:18][CH2:19][OH:20].C(N(CC)CC)C>C(Cl)(Cl)Cl>[OH:20][CH2:19][CH2:18][S:17][CH:2]([CH3:16])[C:3](=[O:15])[C:4](=[N:10][O:11][CH2:12][CH2:13][CH3:14])[C:5]([O:7][CH2:8][CH3:9])=[O:6]

Participants

5

Reactant 3

HCID 15672-MercaptoethanolHCID 8471TriethylamineHCID 53715664HCID 53715664, compound

Product 1

HCID 54314561HCID 54314561, compoundYield 85.1%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Conditions

Temperature
20 °C

Procedure

Ethyl 4 chloro-3-oxo-2-n-propoxyiminovalerate (180.0 g.) was added to a stirred solution of 2-mercaptoethanol (71.6 g.) in chloroform (1.8 l.), and then a solution of triethylamine (93.1 g.) in chloroform (200 ml.) was added to the solution over 5 minutes. The solution was stirred at 20° C. for 80 minutes. After washing the resultant mixture with 10% hydrochloric acid twice, a saturated aqueous solution of sodium bicarbonate twice and water in turn, the solution was dried over magnesium sulfate and concentrated in vacuo to give ethyl 4-(2-hydroxyethylthio)-3-oxo-2-n-propoxyiminovalerate (178.7 g.).

Workup

  1. washAfter washing the resultant mixture with 10% hydrochloric acid twice
  2. dry with materiala saturated aqueous solution of sodium bicarbonate twice and water in turn, the solution was dried over magnesium sulfate
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-42cdc31833a746c981f654f71afade7c
Source dataset
uspto-grants-1985_02
Patent number
US04500709

Reaction notes

Loading…