Hydrochloric Acid → HCID 68599145, compound

HRID 2246096Notes

Reaction equation

HRID 2246096 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[N:7]=[CH:8][S:9][C:10]=1[C:11](OCC)=[O:12])=[O:5])[CH3:2].[BH4-].[Na+].O.Cl>C(O)C>[CH2:1]([O:3][C:4]([C:6]1[N:7]=[CH:8][S:9][C:10]=1[CH2:11][OH:12])=[O:5])[CH3:2]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 4311764Sodium borohydrideHCID 21817133HCID 21817133, compound

Product 1

HCID 68599145HCID 68599145, compoundYield 39.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

4,5-Diethoxycarbonylthiazole (7.13 g) was dissolved in 100 ml of ethanol, 2.20 g of sodium borohydride was added to the solution in an argon atmosphere under ice cooling, and the mixture was stirred at room temperature for 12 hr. Water was added to the reaction solution, the mixture was adjusted to pH 4.5 by the addition of 1 N aqueous hydrochloric acid, and the organic solvent was removed by distillation under the reduced pressure. The remaining aqueous solution was extracted five times with chloroform, was dried over anhydrous magnesium sulfate, was filtered, and was concentrated under the reduced pressure. Ethyl acetate and hexane were added to the concentrate, and the resultant solid was collected by filtration to give 2.29 g of 4-ethoxycarbonyl-5-hydroxymethylthiazole.

Workup

  1. customthe organic solvent was removed by distillation under the reduced pressure
  2. extractionThe remaining aqueous solution was extracted five times with chloroform
  3. dry with materialwas dried over anhydrous magnesium sulfate
  4. filtrationwas filtered
  5. concentrationwas concentrated under the reduced pressure
  6. additionEthyl acetate and hexane were added to the concentrate
  7. filtrationthe resultant solid was collected by filtration

Sources & evidence

ORD record
ord-cfb7bf37eea34f1ca98491dcf7934f82
Source dataset
uspto-grants-2010_03
Patent number
US07687490B2

Reaction notes

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