Ammonia → HCID 21504358, compound

HRID 1288291Notes

Reaction equation

HRID 1288291 reaction equation
[CH2:1]([C:8]1[CH:9]=[C:10]([CH:13]=[CH:14][CH:15]=1)[C:11]#[N:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[ClH:16].[NH3:17]>C(O)C.C(Cl)(Cl)Cl>[ClH:16].[CH2:1]([C:8]1[CH:9]=[C:10]([CH:13]=[CH:14][CH:15]=1)[C:11]([NH2:17])=[NH:12])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 222AmmoniaHCID 313Hydrochloric AcidHCID 21685088HCID 21685088, compound

Product 1

HCID 21504358HCID 21504358, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6212ChloroformSolvent

Conditions

Temperature
0 °C

Procedure

3-Benzylbenzonitrile (83.45 g.; prepared as described by C. R. Hauser, W. Q. Beard and F. N. Jones, J. Org. Chem., 1961, 26, 4790) was dissolved in a mixture of anhydrous ethanol (52 ml.) and anhydrous chloroform (390 ml.). The solution was saturated with anhydrous hydrogen chloride at 0° C. and kept at 0° C. for 3 days. The solvent was evaporated in vacuo and the residue triturated with anhydrous diethyl ether. The solid obtained (78 g.) was treated with saturated anhydrous ethanolic ammonia (600 ml.), and the mixture maintained at 0° C. for 3 days. A small amount of ammonium chloride was filtered off and the filtrate was evaporated in vacuo. The gummy residue was triturated with anhydrous diethyl ether to give a solid, which was filtered off and extracted with hot water. The extract was filtered and evaporated to dryness in vacuo. The resulting residue was recrystallised from a mixture of ethanol and diethyl ether (with the aid of charcoal) to give 3-benzylbenzamidine hydrochloride (30.1 g.), m.p. 170°-180° C.

Workup

  1. customThe solvent was evaporated in vacuo
  2. customthe residue triturated with anhydrous diethyl ether
  3. customThe solid obtained (78 g.)
  4. filtrationA small amount of ammonium chloride was filtered off
  5. customthe filtrate was evaporated in vacuo
  6. customThe gummy residue was triturated with anhydrous diethyl ether
  7. customto give a solid, which
  8. filtrationwas filtered off
  9. extractionextracted with hot water
  10. filtrationThe extract was filtered
  11. customevaporated to dryness in vacuo
  12. customThe resulting residue was recrystallised from a mixture of ethanol and diethyl ether (with the aid of charcoal)

Sources & evidence

ORD record
ord-46b8fa7966554504a36c44e9a5164727
Source dataset
uspto-grants-1976_10
Patent number
US03987160

Reaction notes

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