Hydrochloric Acid → HCID 178433564, compound

HRID 1858505Notes

Reaction equation

HRID 1858505 reaction equation
[SH:1][C:2]1[S:3][C:4]([CH2:8][C:9](OCC)=[O:10])=[C:5]([CH3:7])[N:6]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].O.Cl>O1CCCC1>[OH:10][CH2:9][CH2:8][C:4]1[S:3][C:2]([SH:1])=[N:6][C:5]=1[CH3:7]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 21226445Aluminium lithium hydrideHCID 178470820HCID 178470820, compound

Product 1

HCID 178433564HCID 178433564, compoundYield 50.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
60 °C

Procedure

To a solution of ethyl 2-mercapto-4-methyl-5-thiazole acetate (217 mg) in tetrahydrofuran (5.0 ml) was added lithium aluminum hydride (38 mg) at ice-cooling. After stirring at 60° C. for 2 hours, the mixture was poured into a mixture of tetrahydrofuran and water, and adjusted to pH 3.0 with 1N-hydrochloric acid. The separated organic layer was washed with saturated aqueous sodium chloride solution, dried over magnesium sulfate and evaporated under reduced pressure. The residue was subjected to column chromatography on silica gel (eluent: hexane/ethyl acetate=2/3) to give 5-(2-hydroxyethyl)-2-mercapto-4-methylthiazole (89 mg).

Workup

  1. temperaturecooling
  2. washThe separated organic layer was washed with saturated aqueous sodium chloride solution
  3. dry with materialdried over magnesium sulfate
  4. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-4518fde3206a482e83359cfb7ff129c9
Source dataset
uspto-grants-2000_11
Patent number
US06150351

Reaction notes

Loading…