Acetonitrile → HCID 21327436, compound

HRID 597730Notes

Reaction equation

HRID 597730 reaction equation
[Cl:1]CC(Cl)=O.[N+]([C:9]1[CH:10]=[C:11]([CH2:15]C(N)C)[CH:12]=[CH:13][CH:14]=1)([O-])=O.C(=O)([O-])[O-].[K+].[K+].C(#[N:27])C.[N+:28]([C:31]1[CH:32]=[C:33]([CH2:37][CH:38]([NH:40][C:41](=[O:44])[CH2:42]Cl)[CH3:39])[CH:34]=[CH:35][CH:36]=1)([O-:30])=[O:29]>>[ClH:1].[N+:28]([C:31]1[CH:32]=[C:33]([CH2:37][CH:38]([NH:40][C:41](=[O:44])[CH2:42][NH:27][CH2:15][C:11]2[CH:10]=[CH:9][CH:14]=[CH:13][CH:12]=2)[CH3:39])[CH:34]=[CH:35][CH:36]=1)([O-:30])=[O:29]

Participants

6

Reactant 5

HCID 6342AcetonitrileHCID 6577Chloroacetyl chlorideHCID 11430Potassium CarbonateHCID 19783051HCID 19783051, compoundHCID 213274382-Chloro-N-[1-(3-nitrophenyl)propan-2-yl]acetamide

Product 1

HCID 21327436HCID 21327436, compound

Procedure

7.5 gm of chloroacetyl chloride were added dropwise to a mixture of 18 gm of 1-(3'-nitro-phenyl)-2-amino-propane, 14 gm of potassium carbonate and 150 ml of acetonitrile, whereby the temperature of the mixture rose to 45° C, and the resulting mixture was refluxed for two hours. Thereafter, the reaction mixture was allowed to cool, and then it was diluted with ice water, whereupon 1-(3'-nitro-phenyl)-2-(chloroacetyl-amino)-propane (m.p. 118° -120° C, recrystallized from ethyl acetate/petroleum ether) crystallized out. 17 gm of this compound were added to a mixture of 14 gm of benzylamine and 200 ml of acetonitrile, and the mixture was refluxed for two hours. Thereafter, the benzylamine hydrochloride which had precipitated out was removed by suction filtration, the filtrate was acidified with ethereal hydrochloric acid, and the crystalline precipitate formed thereby was recrystallized from 1 N hydrochloric acid, yielding 11.5 gm of 1-(3'-nitro-phenyl)-2-(benzylaminoacetyl-amino)-propane hydrochloride, m.p. 167° -170° C. This hydrochloride was hydrogenated in methanol in the presence of Raney nickel at atmospheric pressure and room temperature, yielding 1-(3'-aminophenyl)-2-(benzylaminoacetyl-amino)-propane hydrochloride which was dissolved in ethanol, and the solution was admixed with the calculated amount of ethereal hydrochloric acid, yielding the dihydrochloride of the formula ##STR28## which had a melting point of 234° -236° C (decomp.).

Workup

  1. customrose to 45° C
  2. temperaturethe resulting mixture was refluxed for two hours
  3. temperatureto cool
  4. customcrystallized out
  5. addition17 gm of this compound were added to a mixture of 14 gm of benzylamine and 200 ml of acetonitrile
  6. temperaturethe mixture was refluxed for two hours
  7. customThereafter, the benzylamine hydrochloride which had precipitated out
  8. customwas removed by suction filtration
  9. customthe crystalline precipitate formed
  10. customthereby was recrystallized from 1 N hydrochloric acid

Sources & evidence

ORD record
ord-86af8c926ae1479abcc6cc210705863d
Source dataset
uspto-grants-1977_03
Patent number
US04015011

Reaction notes

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