Dimethylamine → HCID 20361456, compound

HRID 1679780Notes

Reaction equation

HRID 1679780 reaction equation
[C:1]([O:8][CH3:9])(=[O:7])[CH2:2][C:3]([O:5][CH3:6])=[O:4].[C:10]([C:14]1[C:19]([OH:20])=[C:18]([CH3:21])[C:17]([CH3:22])=[C:16]([CH2:23]NN(C)C)[CH:15]=1)([CH3:13])([CH3:12])[CH3:11].[CH3:28][O-:29].[Na+].CNC>C1(C)C=CC=CC=1>[C:10]([C:14]1[C:19]([OH:20])=[C:18]([CH3:21])[C:17]([CH3:22])=[C:16]([CH:15]=1)[CH2:23][C:2]([CH2:23][C:16]1[CH:15]=[C:14]([C:10]([CH3:12])([CH3:11])[CH3:13])[C:28]([OH:29])=[C:18]([CH3:19])[C:17]=1[CH3:22])([C:1]([O:8][CH3:9])=[O:7])[C:3]([O:5][CH3:6])=[O:4])([CH3:13])([CH3:12])[CH3:11]

Participants

6

Reactant 4

HCID 674DimethylamineHCID 7943Dimethyl malonateHCID 10942334Sodium MethoxideHCID 57063776HCID 57063776, compound

Product 1

HCID 20361456HCID 20361456, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

6.6 grams of dimethyl malonate (0.05 moles), 23.5 grams of 6-tert.-butyl-2,3-dimethyl-4-(dimethylaminoaminomethyl)phenol (0.10 moles) and 0.5 grams of sodium methylate were charged to 100 ml of toluene at room temperature and heated at reflux for 41/2 hours, dimethylamine being evolved during this period. The reaction mixture cooled to room temperature was made acid with 3N aqueous hydrochloric, the toluene phase being washed with water, the wash water being separated. The desired product was insoluble in the cooled toluene phase and was isolated as white crystals by filtration. After drying and recrystallization from toluene the product melted at 204° to 207° C.

Workup

  1. temperatureheated
  2. waitevolved during this period
  3. washthe toluene phase being washed with water
  4. customthe wash water being separated
  5. customwas isolated as white crystals by filtration
  6. customAfter drying
  7. customrecrystallization from toluene the product melted at 204° to 207° C.

Sources & evidence

ORD record
ord-647652cbc0a144e4abb1b2d01af992b5
Source dataset
uspto-grants-1978_03
Patent number
US04081475

Reaction notes

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