Triethyl orthoacetate → N,N'-bis[phenylcarbamylmethyl]acetamidine hydrochloride

HRID 1863453Notes

Reaction equation

HRID 1863453 reaction equation
[ClH:1].[NH2:2][CH2:3][C:4]([NH:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)=[O:5].[NH2:13][CH2:14][C:15]([NH:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)=[O:16].[C:24](OCC)(OCC)(OCC)[CH3:25]>CO>[ClH:1].[C:7]1([NH:6][C:4]([CH2:3][NH:2][C:24](=[N:13][CH2:14][C:15](=[O:16])[NH:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH3:25])=[O:5])[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

5

Reactant 3

HCID 66221Triethyl orthoacetateHCID 2083842-AminoacetanilideHCID 4587522-Aminoacetanilide hydrochloride

Product 1

HCID 20391596N,N'-bis[phenylcarbamylmethyl]acetamidine hydrochlorideYield 20.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

0.82 Grams (4.13 millimoles) of 2-aminoacetanilide hydrochloride, 0.77 g (4.13 millimoles) of 2-aminoacetanilide (free base) were dissolved in 1.4 milliliters of hot methanol. To this solution was added 0.76 milliliters (0.67 g, 4.13 millimoles) of triethyl orthoacetate. The mixture was heated gently for five minutes. The reaction mixture was cooled and the reaction product precipitated by addition of diethyl ether. The supernatant liquid was decanted, and the precipitate was triturated with ether and collected on a filter. The product was recrystallized from ethanol, and dried to yield about 300 milligrams of N,N'-bis[phenylcarbamylmethyl]acetamidine hydrochloride.

Workup

  1. temperatureThe mixture was heated gently for five minutes
  2. temperatureThe reaction mixture was cooled
  3. customthe reaction product precipitated by addition of diethyl ether
  4. customThe supernatant liquid was decanted
  5. customthe precipitate was triturated with ether
  6. customcollected on a filter
  7. customThe product was recrystallized from ethanol
  8. customdried

Sources & evidence

ORD record
ord-f89d4c4f32e4458ba2289ac3cd12cf9d
Source dataset
uspto-grants-1979_09
Patent number
US04169106

Reaction notes

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