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

HRID 462053Notes

Reaction equation

HRID 462053 reaction equation
C[N+]([CH2:5][C:6]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[NH:8][CH:7]=1)(C)C.[I-].[Cl:16][C:17]([Cl:22])([Cl:21])[C:18]([NH2:20])=[NH:19]>C(O)C>[NH:8]1[C:9]2[C:14](=[CH:13][CH:12]=[CH:11][CH:10]=2)[C:6]([CH2:5][NH:19][C:18](=[NH:20])[C:17]([Cl:22])([Cl:21])[Cl:16])=[CH:7]1

Participants

4

Reactant 2

HCID 356082,2,2-TrichloroethanimidamideHCID 6097052Gramine methiodide

Product 1

HCID 178512121HCID 178512121, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

A solution of gramine methiodide (31.6 g., 0.1 mole) in 250 ml. of ethanol is treated dropwise over a period of 30 minutes with a solution of trichloroacetamidine (16.1 g., 0.1 mole) in 50 ml. of ethanol. The solution is refluxed for 15 minutes, cooled and the solvent removed in vacuo to give a crystalline residue. The residue is partitioned between 150 ml. portions of chloroform and water and the water layer back-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 solution is refluxed for 15 minutes
  2. temperaturecooled
  3. customthe solvent removed in vacuo
  4. customto give a crystalline residue
  5. customThe residue is partitioned between 150 ml
  6. extractionportions of chloroform and water and the water layer back-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-0335a6963ed0421ba689cd0d4ef088f0
Source dataset
uspto-grants-1977_12
Patent number
US04065464

Reaction notes

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