Dimethylformamide → HCID 20567872, compound

HRID 1733295Notes

Reaction equation

HRID 1733295 reaction equation
[CH3:1][N:2]1[CH:6]=[CH:5][N:4]=[C:3]1[NH:7][C:8](=O)[CH3:9].[CH3:11][N:12](C)[CH:13]=O.[H-].[Na+].Cl.CN(CCCl)C>C(O)C>[CH3:11][N:12]([CH3:13])[CH2:9][CH2:8][NH:7][C:3]1[N:2]([CH3:1])[CH:6]=[CH:5][N:4]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 24758Sodium hydride2×HCID 11636816N,N-Dimethylaminoethyl chloride hydrochlorideHCID 12628731HCID 12628731, compound

Product 1

HCID 20567872HCID 20567872, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Dissolve 9.5 g. (0.0683 moles) of N-(1-methyl-2-imidazolyl)acetamide in 150 ml. of dimethylformamide under nitrogen. 3.375 g. (0.75 moles) of sodium hydride 50% suspension is added and stirred at 30°-40° C. until gas evolution ceases. The reaction mixture is cooled to room temperature and an additional 3.375 g. of sodium hydride added along with 10.8 g. (0.075 moles) of dimethylaminoethyl chloride hydrochloride. The reaction mixture is stirred at 30°-45° C. until gas evolution ceases and at 50° C. for 1/2 hour and at 90° C. for 2 hours. The mixture is cooled to room temperature, 20 ml. of ethanol added and the mixture evaporated in vacuo. The residue is taken up in 150 ml. of 6 N hydrochloric acid and refluxed for 24 hours. The aqueous acid layer is extracted with hexane and then neutralized with 50 ml. of saturated sodium carbonate. The aqueous layer is extracted with chloroform (100 ml., 10 times) the organic layer washed with saturated sodium chloride, and evaporated to dryness affording 8.8 g. of oil identified as N,N-dimethyl-N'-(1-methyl-2-imidaziolyl)-1,2-ethane-diamine, which is used as in the next step.

Workup

  1. dissolutionDissolve 9.5 g
  2. stirringThe reaction mixture is stirred at 30°-45° C. until gas evolution ceases and at 50° C. for 1/2 hour and at 90° C. for 2 hours
  3. temperatureThe mixture is cooled to room temperature
  4. customthe mixture evaporated in vacuo
  5. temperatureof 6 N hydrochloric acid and refluxed for 24 hours
  6. extractionThe aqueous acid layer is extracted with hexane
  7. extractionThe aqueous layer is extracted with chloroform (100 ml., 10 times) the organic layer
  8. washwashed with saturated sodium chloride
  9. customevaporated to dryness
  10. customaffording 8.8 g

Sources & evidence

ORD record
ord-d8c66b807a1440b690d264d7d7b178f4
Source dataset
uspto-grants-1980_12
Patent number
US04241072

Reaction notes

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