Acetamidine monohydrochloride → HCID 136102355, compound

HRID 1440448Notes

Reaction equation

HRID 1440448 reaction equation
CC[O-].[Na+].Cl.[C:6]([NH2:9])(=[NH:8])[CH3:7].[F:10][C:11]([F:27])([F:26])[C:12]([CH:14]([CH2:20][C:21]([O:23][CH2:24][CH3:25])=[O:22])[C:15](OCC)=[O:16])=O.CCOCC.CCCCCC>CCO>[CH3:7][C:6]1[NH:9][C:15](=[O:16])[C:14]([CH2:20][C:21]([O:23][CH2:24][CH3:25])=[O:22])=[C:12]([C:11]([F:10])([F:27])[F:26])[N:8]=1

Participants

6

Reactant 4

HCID 67170Acetamidine monohydrochlorideHCID 2723922Sodium ethoxideHCID 11346247Butanedioic acid, (trifluoroacetyl)-, diethyl esterHCID 21584099Diethylether hexane

Product 1

HCID 136102355HCID 136102355, compoundYield 27%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of NaOEt (0.074 mol) in EtOH (prepared from 1.7 g of Na and 75 mL of EtOH), acetamidine hydrochloride (3.5 g, 0.037 mol), and diethyl 2-trifluoroacetylsuccinate (10.0 g, 0.037 mol) was heated under reflux for 20 h. The mixture was concentrated, taken up in water, acidified to pH 4 with conc. HCl, and extracted with EtOAc. The extracts were washed with brine, dried (MgSO4), and concentrated to give an oily solid. Trituration with ether/hexane gave 2.63 g (27%) of product as a white solid. An analytical sample was recrystallized from ether/hexane, mp 108°-110° C.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 20 h
  3. concentrationThe mixture was concentrated
  4. extractionextracted with EtOAc
  5. washThe extracts were washed with brine
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated
  8. customto give an oily solid

Sources & evidence

ORD record
ord-844115b5b89c48eca5bcc16559849766
Source dataset
uspto-grants-1996_03
Patent number
US05498776

Reaction notes

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