Dimethylcarbamoyl Chloride → HCID 20339667, compound

HRID 1395535Notes

Reaction equation

HRID 1395535 reaction equation
[CH3:1][N:2]([CH3:16])[CH2:3][CH2:4][CH2:5][CH2:6][NH:7][C:8]1[CH:13]=[C:12]([CH3:14])[CH:11]=[C:10]([CH3:15])[N:9]=1.[H-].[Na+].[CH3:19][N:20]([CH3:24])[C:21](Cl)=[O:22]>C1(C)C=CC=CC=1>[CH3:19][N:20]([CH3:24])[C:21]([N:7]([CH2:6][CH2:5][CH2:4][CH2:3][N:2]([CH3:1])[CH3:16])[C:8]1[CH:13]=[C:12]([CH3:14])[CH:11]=[C:10]([CH3:15])[N:9]=1)=[O:22]

Participants

5

Reactant 3

HCID 6598Dimethylcarbamoyl ChlorideHCID 24758Sodium hydrideHCID 20339481HCID 20339481, compound

Product 1

HCID 20339667HCID 20339667, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

To 2-(4-dimethylaminobutylamino)-4,6-dimethylpyridine (3.7 g. 0.00168 mole) dissolved in toluene (150 ml) is added sodium hydride in mineral oil (50%) (0.96 g., 0.002 mole. The mixture is refluxed with stirring under nitrogen for 31/2 hours, cooled to 35°, and dimethylcarbamoyl chloride (2.15 g., 0.002 mole) in toluene (25 ml) is added. The mixture is then refluxed for 18 hours, cooled and extracted with dilute hydrochloric acid. The aqueous extracts are made alkaline with 10 N sodium hydroxide and extracted with diethyl ether then methylene chloride. The combined organic extracts are washed with brine, dried (sodium sulfate) and concentrated under vacuum. The residue is taken up in diethyl ether, filtered from insoluble matter and the filtrate concentrated. The residue is distilled and the product, a hygroscopic oil, is collected at 138°-141°/0.3 mm.

Workup

  1. temperatureThe mixture is refluxed
  2. temperaturecooled to 35°
  3. temperatureThe mixture is then refluxed for 18 hours
  4. temperaturecooled
  5. extractionextracted with dilute hydrochloric acid
  6. extractionextracted with diethyl ether
  7. washThe combined organic extracts are washed with brine
  8. dry with materialdried (sodium sulfate)
  9. concentrationconcentrated under vacuum
  10. filtrationfiltered from insoluble matter
  11. concentrationthe filtrate concentrated
  12. distillationThe residue is distilled
  13. customthe product, a hygroscopic oil, is collected at 138°-141°/0.3 mm

Sources & evidence

ORD record
ord-9c1ab981d47f43f88cd09fc5b7926330
Source dataset
uspto-grants-1980_05
Patent number
US04203988

Reaction notes

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