Dimethylamine → HCID 20033684, compound

HRID 231696Notes

Reaction equation

HRID 231696 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][CH2:10][S:11]([C:14]2[S:18][C:17]([S:19]([NH2:22])(=[O:21])=[O:20])=[CH:16][CH:15]=2)(=[O:13])=[O:12])=[CH:4][CH:3]=1.C=O.[CH3:25][NH:26][CH3:27].CO.[CH:30](Cl)(Cl)Cl>C(O)C>[CH3:25][N:26]([CH2:30][C:7]1[CH:6]=[C:5]([CH2:8][CH2:9][CH2:10][S:11]([C:14]2[S:18][C:17]([S:19]([NH2:22])(=[O:20])=[O:21])=[CH:16][CH:15]=2)(=[O:12])=[O:13])[CH:4]=[CH:3][C:2]=1[OH:1])[CH3:27]

Participants

6

Reactant 4

HCID 674DimethylamineHCID 712FormaldehydeHCID 20033706HCID 20033706, compoundHCID 21584188Chloroform methanol

Product 1

HCID 20033684HCID 20033684, compoundYield 57%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of product from Step C, (1.2 g, 3.3 mmol) in ethanol (16.5 ml) was added formaldehyde (0.3 ml, 37% in water, 3.6 mmol) and dimethylamine (0.8 ml, 40% in water, 6.6 mmol). The reaction was refluxed for 3 hours and then stirred at room temperature overnight. The solution was concentrated, 3N HCl added and extracted with ethyl acetate. The aqueous phase was made basic with saturated bicarbonate solution and extracted with ethyl acetate. Drying and solvent evaporation gave and oil (1.1 g). Column chromatography (silica gel, 5% methanol-CHCl3) gave the title compound (0.8 g, 57%).

Workup

  1. temperatureThe reaction was refluxed for 3 hours
  2. concentrationThe solution was concentrated
  3. addition3N HCl added
  4. extractionextracted with ethyl acetate
  5. extractionextracted with ethyl acetate
  6. customDrying
  7. customsolvent evaporation
  8. customgave

Sources & evidence

ORD record
ord-36e5f434ec2d4d1392bf89ce74d8bb4d
Source dataset
uspto-grants-1989_07
Patent number
US04847289

Reaction notes

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