Sodium hydride → HCID 12791198, compound

HRID 1733296Notes

Reaction equation

HRID 1733296 reaction equation
[CH3:1][C:2]1[N:3]=[C:4]([NH:8][C:9](=O)[CH3:10])[S:5][C:6]=1[CH3:7].[H-].[Na+].Cl.[CH3:15][N:16](CCCl)[CH3:17]>CN(C)C=O>[CH3:15][N:16]([CH3:17])[CH2:10][CH2:9][NH:8][C:4]1[S:5][C:6]([CH3:7])=[C:2]([CH3:1])[N:3]=1

Participants

5

Reactant 3

HCID 24758Sodium hydride2×HCID 3821943HCID 3821943, compoundHCID 11636816N,N-Dimethylaminoethyl chloride hydrochloride

Product 1

HCID 12791198HCID 12791198, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

Dissolve 30.0 g. (0.176 moles) of N-(4,5-dimethyl-2-thiazolyl) acetamide in 375 ml. of dimethylformamide under nitrogen followed by 7.7 g. of 50% sodium hydride in 2 portions at room temperature. When gas evolution ceases, 27.5 g. (0.191 moles) of dimethylaminoethylchloride hydrochloride is added along with 8.35 g. of 50% sodium hydride. The mixture is stirred at 60°-70° C. for 1/2 hour, 90° C. for 2 hours, cooled to room temperature, and concentrated in vacuo. The residue is taken up in 200 ml. of 6 N hydrochloric acid and refluxed for 24 hours. The mixture is extracted with hexane and made basic with sodium hydroxide with cooling. The aqueous layer is extracted with methylene chloride, the organic layer washed with saturated sodium chloride, dried over sodium sulfate and evaporated. The residue is distilled and the fraction boiling at 110°-113° C./0.7 mm. of Hg. collected (29.2 g.) and identified as N,N-dimethyl-N'-(4,5-dimethyl-2-thiazolyl)-1,2-ethanediamine.

Workup

  1. dissolutionDissolve 30.0 g
  2. customat room temperature
  3. temperaturecooled to room temperature
  4. concentrationconcentrated in vacuo
  5. temperatureof 6 N hydrochloric acid and refluxed for 24 hours
  6. extractionThe mixture is extracted with hexane
  7. temperaturewith cooling
  8. extractionThe aqueous layer is extracted with methylene chloride
  9. washthe organic layer washed with saturated sodium chloride
  10. dry with materialdried over sodium sulfate
  11. customevaporated
  12. distillationThe residue is distilled
  13. customcollected (29.2 g.)

Sources & evidence

ORD record
ord-7d185bdc048b468bb97e380aa0c64271
Source dataset
uspto-grants-1980_12
Patent number
US04241072

Reaction notes

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