2-Mercaptoethanol → HCID 178472916, compound

HRID 615745Notes

Reaction equation

HRID 615745 reaction equation
Br[CH:2]([CH3:13])[C:3](=[O:12])[C:4](=[N:10][OH:11])[C:5]([O:7][CH2:8][CH3:9])=[O:6].[SH:14][CH2:15][CH2:16][OH:17].C(N(CC)CC)C>C(Cl)(Cl)Cl>[OH:17][CH2:16][CH2:15][S:14][CH:2]([CH3:13])[C:3](=[O:12])[C:4](=[N:10][OH:11])[C:5]([O:7][CH2:8][CH3:9])=[O:6]

Participants

5

Reactant 3

HCID 15672-MercaptoethanolHCID 8471TriethylamineHCID 178472907HCID 178472907, compound

Product 1

HCID 178472916HCID 178472916, compoundYield 78.5%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

A solution of ethyl 4-bromo-2-hydroxyimino-3-oxovalerate (50 g.) in chloroform (100 ml) was added dropwise to a stirred solution of 2-mercaptoethanol (20.5 g.) and triethylamine (26.6 g.) in chloroform (100 ml) at room temperature over 1.5 hours, and stirred at the same temperature for 2 hours. After removing chloroform from the resultant solution in vacuo, water (600 ml) and ethyl acetate (600 ml) were added to the residue and adjusted to pH 1.0 with conc.hydrochloric acid. The ethyl acetate layer was separated, washed with water (200 ml), dried over magnesium sulfate and then concentrated in vacuo to give ethyl 4-(2-hydroxyethylthio)-2-hydroxyimino-3-oxovalerate (38.8 g.).

Workup

  1. customAfter removing chloroform from the resultant solution in vacuo, water (600 ml) and ethyl acetate (600 ml)
  2. additionwere added to the residue
  3. customThe ethyl acetate layer was separated
  4. washwashed with water (200 ml)
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-656febc6cedb48488ed979e76bb17c64
Source dataset
uspto-grants-1985_02
Patent number
US04500709

Reaction notes

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