Dimethylcarbamoyl Chloride → N,N-Dimethyl-N'-(2-dimethylaminoethyl)-N'-(4,6-dimethyl-2-pyridyl)urea Dihydrochloride

HRID 1395528Notes

Reaction equation

HRID 1395528 reaction equation
[CH3:1][N:2]([CH3:14])[CH2:3][CH2:4][NH:5][C:6]1[CH:11]=[C:10]([CH3:12])[CH:9]=[C:8]([CH3:13])[N:7]=1.C(N(CC)CC)C.[CH3:22][N:23]([CH3:27])[C:24]([Cl:26])=[O:25]>C1C=CC=CC=1>[ClH:26].[ClH:26].[CH3:22][N:23]([CH3:27])[C:24]([N:5]([CH2:4][CH2:3][N:2]([CH3:14])[CH3:1])[C:6]1[CH:11]=[C:10]([CH3:12])[CH:9]=[C:8]([CH3:13])[N:7]=1)=[O:25]

Participants

5

Reactant 3

HCID 6598Dimethylcarbamoyl ChlorideHCID 8471TriethylamineHCID 128576222-(2-Dimethylaminoethylamino)-4,6-dimethylpyridine

Product 1

HCID 12857640N,N-Dimethyl-N'-(2-dimethylaminoethyl)-N'-(4,6-dimethyl-2-pyridyl)urea DihydrochlorideYield 144.9%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

2-(2-Dimethylaminoethylamino)-4,6-dimethylpyridine (7.73 g, 0.04 mole) and triethylamine (4.8 g, 0.048 mole) are dissolved in 200 ml of anhydrous benzene. Dimethyl carbamoyl chloride (4.85 g, 0.045 mole) is added, the mixture stirred at room temperature for 2 hours and then refluxed four hours. After cooling and dilution with 200 ml of diethyl ether, the triethylamine hydrochloride is filtered off and the filtrate concentrated under vacuum. For purification the crude product is taken up in 200 ml diethyl ether and filtered thru Super-Cel. On addition of ethanolic hydrogen chloride to the filtrate, the product crystallizes and is filtered off to obtain 11 g of solid, m.p. 204°. Recrystallization from 150 ml ethanol and 250 ml diethyl ether yields 10.29 g, m.p. 205°-206° C. (d).

Workup

  1. temperaturerefluxed four hours
  2. temperatureAfter cooling
  3. filtrationdilution with 200 ml of diethyl ether, the triethylamine hydrochloride is filtered off
  4. concentrationthe filtrate concentrated under vacuum
  5. customFor purification the crude product
  6. filtrationfiltered
  7. additionOn addition of ethanolic hydrogen chloride to the filtrate
  8. customthe product crystallizes
  9. filtrationis filtered off

Sources & evidence

ORD record
ord-427bab30ae7540f1a8bafa8c6b47b734
Source dataset
uspto-grants-1980_05
Patent number
US04203988

Reaction notes

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