Dimethylamine → HCID 20368563, compound

HRID 616647Notes

Reaction equation

HRID 616647 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4](/[C:9](=[CH:15]\[CH3:16])/[C:10]([O:12][CH2:13][CH3:14])=[O:11])[CH:5]=[CH:6][C:7]=1[Cl:8].C(O)C.[CH3:20][NH:21][CH3:22]>C(O)(=O)C>[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]([CH:15]([N:21]([CH3:22])[CH3:20])[CH3:16])[C:10]([O:12][CH2:13][CH3:14])=[O:11])[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

5

Reactant 3

HCID 674DimethylamineHCID 702EthanolHCID 20368521HCID 20368521, compound

Product 1

HCID 20368563HCID 20368563, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
50 °C

Procedure

In a Parr bomb containing 45 g. of ethyl 2-(3,4-dichlorophenyl)crotonate in 250 ml. of ethanol add 100 ml. of aqueous 33 percent (w/v) dimethylamine and 0.8 ml. of acetic acid. The mixture is maintained with stirring at 50° C for 10 hours, then the solvent is evaporated in vacuo and the residue, after suspension in water, is extracted several times with ether. After evaporation of the dried organic layer, 60 g. of the title compound is obtained which boils at 124° C/0.2 mm Hg. The product is an approximately 50:50 mixture of the two stereoisomers

Workup

  1. additionIn a Parr bomb containing 45 g
  2. temperatureThe mixture is maintained
  3. customthe solvent is evaporated in vacuo
  4. extractionthe residue, after suspension in water, is extracted several times with ether
  5. customAfter evaporation of the dried organic layer, 60 g

Sources & evidence

ORD record
ord-2f9151afcff5452289c6ed17299d4cab
Source dataset
uspto-grants-1978_02
Patent number
US04075241

Reaction notes

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