Water → HCID 13344846, compound

HRID 485045Notes

Reaction equation

HRID 485045 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH3:7][N:8]([CH2:18][C:19]#[CH:20])[C:9]1[S:10][CH:11]=[C:12]([C:14](OC)=[O:15])[N:13]=1.O>O1CCCC1>[CH3:7][N:8]([CH2:18][C:19]#[CH:20])[C:9]1[S:10][CH:11]=[C:12]([CH2:14][OH:15])[N:13]=1

Participants

5

Reactant 3

HCID 962WaterHCID 13344843HCID 13344843, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 13344846HCID 13344846, compoundYield 86.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Lithium aluminum hydride (900 mg) was added to anhydrous tetrahydrofuran (20 ml) and a solution of 2-(N-methyl-2-propynylamino)-4-methoxycarbonylthiazole (h) (5.0 g) in tetrahydrofuran (30 ml) was added dropwise thereto with stirring under ice-cooling. The mixture was refluxed for 2 hours, to which water was carefully added under ice-cooling, and evaporated to remove the tetrahydrofuran. The residue was extracted with chloroform. The extract was washed with water, dried and recrystallized from ether-hexane to give 2-(N-methyl-2-propynylamino)-4-hydroxymethylthiazole (i) (3.75 g, yield 86.5%): mp. 69°-70° C.

Workup

  1. temperaturecooling
  2. additionwas carefully added under ice-
  3. temperaturecooling
  4. customevaporated
  5. customto remove the tetrahydrofuran
  6. extractionThe residue was extracted with chloroform
  7. washThe extract was washed with water
  8. customdried
  9. customrecrystallized from ether-hexane

Sources & evidence

ORD record
ord-3603e4c08e92433fa43e250b1ace144c
Source dataset
uspto-grants-1985_08
Patent number
US04535088

Reaction notes

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