HCID 13344847, compound → HCID 20271334, compound

HRID 485048Notes

Reaction equation

HRID 485048 reaction equation
[CH3:1][N:2]([CH2:13][C:14]#[CH:15])[C:3]1[S:4][CH:5]=[C:6]([C:8]([N:10]([CH3:12])[CH3:11])=O)[N:7]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>O1CCCC1>[CH3:1][N:2]([CH2:13][C:14]#[CH:15])[C:3]1[S:4][CH:5]=[C:6]([CH2:8][N:10]([CH3:12])[CH3:11])[N:7]=1

Participants

4

Reactant 2

HCID 13344847HCID 13344847, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 20271334HCID 20271334, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2-(N-Methyl-2-propynylamino)-4-dimethylaminocarbonylthiazole (k) (474 mg) was dissolved in tetrahydrofuran (15 ml) and lithium aluminium hydride (250 mg) was added thereto at room temperature with stirring. The mixture was refluxed for 1 hour and, after decomposition of the excess lithium aluminium hydride with water, evaporated to remove the tetrahydrofuran. The residue was extracted with chloroform. The extract was washed with water, dried and evaporated to remove the solvent. The residue was applied to column chromatography on silica gel (10 g) to give 2-(N-methyl-2-propynylamino)-4-dimethylaminomethylthiazole (1) from chloroform-methanol (10:1) eluate as an oil (374 mg).

Workup

  1. temperatureThe mixture was refluxed for 1 hour
  2. customafter decomposition of the excess lithium aluminium hydride with water, evaporated
  3. customto remove the tetrahydrofuran
  4. extractionThe residue was extracted with chloroform
  5. washThe extract was washed with water
  6. customdried
  7. customevaporated
  8. customto remove the solvent

Sources & evidence

ORD record
ord-98bacb7979b74d28bdcb6842bb729fae
Source dataset
uspto-grants-1985_08
Patent number
US04535088

Reaction notes

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