Hydrochloric Acid → HCID 13209659, compound

HRID 544643Notes

Reaction equation

HRID 544643 reaction equation
C[O:2][C:3]([CH2:5][S:6][C:7]1[S:8][C:9]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[C:10]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[N:11]=1)=O.[H-].[Al+3].[Li+].[H-].[H-].[H-].O.Cl>C(OCC)C>[OH:2][CH2:3][CH2:5][S:6][C:7]1[S:8][C:9]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[C:10]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[N:11]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 20458357HCID 20458357, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 13209659HCID 13209659, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

4.93 g of 2-methoxycarbonylmethylthio-4,5-bis-phenylthiazole are added dropwise in the course of 30 minutes, while stirring, to a solution, cooled to from 0° to 5°, of 0.575 g of lithium aluminium hydride in 25 ml of diethyl ether. The mixture is then stirred for 1 hour, first of all 0.6 ml and then a further 50 ml of water are cautiously added, the mixture is acidified with N hydrochloric acid, the ether layer is separated off and the aqueous phase is subsequently washed with diethyl ether. The ethereal solutions are combined, dried over magnesium sulphate and concentrated to dryness by evaporation. The residue is dissolved in toluene and purified by chromatography over 90 g of silica gel. The fractions eluted with toluene/ethyl acetate are combined and concentrated by evaporation under reduced pressure. 2-(2-Hydroxyethylthio)-4,5-bis-phenylthiazole having a melting point of 77°-79° is obtained.

Workup

  1. stirringThe mixture is then stirred for 1 hour, first of all 0.6 ml
  2. customthe ether layer is separated off
  3. washthe aqueous phase is subsequently washed with diethyl ether
  4. dry with materialdried over magnesium sulphate
  5. concentrationconcentrated to dryness by evaporation
  6. dissolutionThe residue is dissolved in toluene
  7. custompurified by chromatography over 90 g of silica gel
  8. washThe fractions eluted with toluene/ethyl acetate
  9. concentrationconcentrated by evaporation under reduced pressure

Sources & evidence

ORD record
ord-336b2213337945be950fd94f2a7cc836
Source dataset
uspto-grants-1984_05
Patent number
US04451471

Reaction notes

Loading…