2,2,2-Trichloroethanimidamide → HCID 178512121, compound

HRID 462054Notes

Reaction equation

HRID 462054 reaction equation
Cl[CH2:2][C:3]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[NH:5][CH:4]=1.[Cl:12][C:13]([Cl:18])([Cl:17])[C:14]([NH2:16])=[NH:15]>CCOCC>[NH:5]1[C:6]2[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=2)[C:3]([CH2:2][NH:16][C:14](=[NH:15])[C:13]([Cl:18])([Cl:17])[Cl:12])=[CH:4]1

Participants

4

Reactant 2

HCID 356082,2,2-TrichloroethanimidamideHCID 137608333-(Chloromethyl)-1H-indole

Product 1

HCID 178512121HCID 178512121, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

A solution of 8.3 g. (0.05 mole) of 3-(chloromethyl) indole in 30 ml. of ether is mixed with a solution of 8.1 g. (0.05 mole) of trichloroacetamidine, also in ether. The mixture is heated at reflux for 3 hours, and concentrated in vacuo to an oil. This is taken up in warm chloroform, filtered, and the chloroform extracts washed first with water and then with dilute hydrochloric acid. The aqueous layers are combined, made basic with a saturated aqueous solution of sodium bicarbonate and the product extracted with chloroform. The combined chloroform extracts are washed with water, dried over magnesium sulfate, filtered and concentrated in vacuo affording N-(3-indolylmethyl) trichloroacetamidine m.p. 135.5 to 138.5 after recrystallization from benzene/hexane.

Workup

  1. temperatureThe mixture is heated
  2. temperatureat reflux for 3 hours
  3. concentrationconcentrated in vacuo to an oil
  4. filtrationfiltered
  5. washthe chloroform extracts washed first with water
  6. extractionthe product extracted with chloroform
  7. washThe combined chloroform extracts are washed with water
  8. dry with materialdried over magnesium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-58445d37348a49ee8c1bf33fabe0b229
Source dataset
uspto-grants-1977_12
Patent number
US04065464

Reaction notes

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