Dichlone → HCID 13934790, compound

HRID 1788904Notes

Reaction equation

HRID 1788904 reaction equation
[CH3:1][NH:2][CH2:3][CH2:4][N:5]([CH3:13])[CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[Cl:14][C:15]1[C:16](=[O:27])[C:17]2[C:22]([C:23](=[O:26])[C:24]=1[Cl:25])=[CH:21][CH:20]=[CH:19][CH:18]=2>C(O)C>[ClH:14].[Cl:25][C:24]1[C:23](=[O:26])[C:22]2[C:17]([C:16](=[O:27])[C:15]=1[N:2]([CH3:1])[CH2:3][CH2:4][N:5]([CH3:13])[CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)=[CH:18][CH:19]=[CH:20][CH:21]=2

Participants

4

Reactant 2

HCID 8342DichloneHCID 66016N-Benzyl-N,N'-dimethylethylenediamine

Product 1

HCID 13934790HCID 13934790, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
-10 °C

Procedure

A 4.5 g portion of methyl 2-[methyl(phenylmethyl)amino]ethylamine was added to a stirred slurry of 5.6 g of 2,3-dichloro-1,4-naphthoquinone in 150 ml of absolute ethanol. Stirring was continued for 16 hours, then the mixture was heated at reflux for one hour and filtered while hot. The mixture was then cooled at -10° C. and filtered. This filtrate was diluted with 100 ml of ether and cooled at -10° C. The resulting precipitate was collected, washed with ether and dried in vacuo at 100° C., giving 3.5 g of the desired product as orange crystals, mp 188°-190° C. (dec.).

Workup

  1. temperaturethe mixture was heated
  2. temperatureat reflux for one hour
  3. filtrationfiltered while hot
  4. filtrationfiltered
  5. additionThis filtrate was diluted with 100 ml of ether
  6. temperaturecooled at -10° C
  7. customThe resulting precipitate was collected
  8. washwashed with ether
  9. customdried in vacuo at 100° C.

Sources & evidence

ORD record
ord-1eafa52968e943938f9fb0c465258a6f
Source dataset
uspto-grants-1987_08
Patent number
US04686220

Reaction notes

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