2-Mercaptoethanol → HCID 178472918, compound

HRID 1834796Notes

Reaction equation

HRID 1834796 reaction equation
Cl[CH2:2][C:3](=[O:12])[C:4](=[N:10][OH:11])[C:5]([O:7][CH2:8][CH3:9])=[O:6].[SH:13][CH2:14][CH2:15][OH:16].C(N(CC)CC)C>C(Cl)(Cl)Cl>[OH:16][CH2:15][CH2:14][S:13][CH2:2][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 178472915HCID 178472915, compound

Product 1

HCID 178472918HCID 178472918, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Conditions

Temperature
20 °C

Procedure

Ethyl 4-chloro-2-hydroxyimino-3-oxo-butyrate (340 g.) is dissolved in chloroform (1.5 liters) and 2-mercapto-ethanol (126 cc.) is then added. Triethylamine (248 cc.) dissolved in chloroform (1 liter) is added to the resulting solution at about 20° C., over the course of 30 minutes. The reagents are left in contact for 15 hours whilst stirring at about 20° C. Then the reaction mixture is washed with water (200 cc.) followed by 2 N hydrochloric acid (200 cc.) and finally four times with water (a total of 1 liter). The organic phase is dried over sodium sulphate treated with decolourising charcoal, filtered and concentrated to dryness under reduced pressure (20 mm.Hg). Ethyl 4-(2-hydroxy-ethylthio)-2-hydroxyimino-3-oxo-butyrate (321 g.) is thus obtained in the form of an oil which gradually solidifies.

Workup

  1. additionis added to the resulting solution at about 20° C., over the course of 30 minutes
  2. washThen the reaction mixture is washed with water (200 cc.)
  3. dry with materialThe organic phase is dried over sodium sulphate
  4. additiontreated with decolourising charcoal
  5. filtrationfiltered
  6. concentrationconcentrated to dryness under reduced pressure (20 mm.Hg)

Sources & evidence

ORD record
ord-176d1402f0934ddd8a5419367dc68c22
Source dataset
uspto-grants-1978_01
Patent number
US04071531

Reaction notes

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