Dimethylcarbamoyl Chloride → HCID 20303058, compound

HRID 1732876Notes

Reaction equation

HRID 1732876 reaction equation
[CH3:1][N:2]([CH3:6])[C:3](Cl)=[O:4].[CH2:7]([N:9]([CH2:22][CH3:23])[C:10]([N:12]1[CH2:17][CH2:16][N:15]([CH2:18][CH2:19][NH:20][CH3:21])[CH2:14][CH2:13]1)=[O:11])[CH3:8].C(N(CC)CC)C>C1(C)C=CC=CC=1>[CH3:1][N:2]([CH3:6])[C:3]([N:20]([CH3:21])[CH2:19][CH2:18][N:15]1[CH2:16][CH2:17][N:12]([C:10](=[O:11])[N:9]([CH2:22][CH3:23])[CH2:7][CH3:8])[CH2:13][CH2:14]1)=[O:4]

Participants

5

Reactant 3

HCID 6598Dimethylcarbamoyl ChlorideHCID 8471TriethylamineHCID 20303056HCID 20303056, compound

Product 1

HCID 20303058HCID 20303058, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Conditions

Temperature
100 °C

Procedure

5.4 g (0.05 mole) of dimethyl carbamic acid chloride dissolved in 20 cc. of toluene are added dropwise with stirring at room temperature to a solution of 12.1 g (0.05 mole) of 1-diethylcarbamoyl-4-(2-methylamino ethyl)-piperazine and 5.1 g (0.05 mole) of triethylamine in 40 cc. of toluene. Thereafter, the reaction mixture is stirred for another hour at about 100° C. The reaction mixture is cooled and the precipitated triethylamine hydrochloride is filtered off with suction and the filtrate is evaporated. The residue is dissolved in 150 cc. of ether, the ethereal solution is washed twice with 150 cc. of 5 n NaOH each time and the resulting solution is dried over anhydrous Na2SO4. Upon evaporation of the ether, 15.3 g (97.6% of the theoretical) of the oily crude urea are obtained.

Workup

  1. temperatureThe reaction mixture is cooled
  2. filtrationthe precipitated triethylamine hydrochloride is filtered off with suction
  3. customthe filtrate is evaporated
  4. dissolutionThe residue is dissolved in 150 cc
  5. washof ether, the ethereal solution is washed twice with 150 cc
  6. dry with materialof 5 n NaOH each time and the resulting solution is dried over anhydrous Na2SO4
  7. customUpon evaporation of the ether, 15.3 g (97.6% of the theoretical) of the oily crude urea
  8. customare obtained

Sources & evidence

ORD record
ord-5005cd4fae3d4c98a781cc0299dc42e6
Source dataset
uspto-grants-1980_12
Patent number
US04239761

Reaction notes

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