Hydrochloric Acid → 2-(Dimethylaminomethyl)-4-(2-aminoethylthiomethyl)thiazole

HRID 1758619Notes

Reaction equation

HRID 1758619 reaction equation
[C:1]([N:10]([CH2:12][C:13]1[S:14][CH:15]=[C:16]([CH2:18][S:19][CH2:20][CH2:21][NH2:22])[N:17]=1)[CH3:11])(OC1C=CC=CC=1)=O.[H-].[Al+3].[Li+].[H-].[H-].[H-].[OH-].[Na+].Cl>O1CCCC1.C(O)C.C(OCC)C.O>[CH3:11][N:10]([CH2:12][C:13]1[S:14][CH:15]=[C:16]([CH2:18][S:19][CH2:20][CH2:21][NH2:22])[N:17]=1)[CH3:1]

Participants

9

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 13102897HCID 13102897, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 109773182-(Dimethylaminomethyl)-4-(2-aminoethylthiomethyl)thiazoleYield 64.2%

Reagents, catalysts & solvents 4

HCID 702EthanolSolventHCID 962WaterSolvent2×HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 2-{[2-(N-Carbophenoxy-N-methylamino)methyl-4-thiazolyl]methylthio}ethylamine (0.50 g; 1.48 mmoles) [prepared in Step D] in 10 ml of dry tetrahydrofuran under a nitrogen atmosphere was added lithium aluminum hydride (0.17 g; 4.48 mmoles) and the mixture was heated at reflux temperature for 0.5 hour. An additional 10 ml of tetrahydrofuran was added and heating was continued for 3 hours. The reaction mixture was treated with 0.17 ml of H2O, 0.17 ml of 15% aqueous NaOH and 0.51 ml of H2O, and filtered through Celite and dried. The filtrate was filtered and evaporated under reduced pressure to give an oil which was dissolved in absolute ethanol, diluted with diethyl ether and acidified with dry HCl. The hydroscopic hydrochloride salt of the title compound was collected and partitioned between aqueous 2.5 N NaOH and methylene chloride. The organic phase was washed with water, dried and filtered. The filtrate was evaporated under reduced pressure to give the free base of the title compound as an oil (0.22 g; 0.95 mmole) which was combined with anhydrous oxalic acid (0.24 g; 1.90 mmole) in 30 ml of hot acetonitrile. The mixture was evaporated from hot absolute ethanol to yield the title compound the bis-oxalate, mp 168°-171°.

Workup

  1. temperaturethe mixture was heated
  2. temperatureat reflux temperature for 0.5 hour
  3. temperatureheating
  4. filtrationfiltered through Celite
  5. customdried
  6. filtrationThe filtrate was filtered
  7. customevaporated under reduced pressure
  8. customto give an oil which
  9. customThe hydroscopic hydrochloride salt of the title compound was collected
  10. custompartitioned between aqueous 2.5 N NaOH and methylene chloride
  11. washThe organic phase was washed with water
  12. customdried
  13. filtrationfiltered
  14. customThe filtrate was evaporated under reduced pressure

Sources & evidence

ORD record
ord-42dc79037fe442c7b061b3d58dce888d
Source dataset
uspto-grants-1983_02
Patent number
US04374248

Reaction notes

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