Hydrochloric Acid → HCID 20040544, compound

HRID 1763084Notes

Reaction equation

HRID 1763084 reaction equation
[Cl:1][C:2]1[C:14]([Cl:15])=[C:13]([CH2:16][C:17]#[N:18])[CH:12]=[C:11]2[C:3]=1[C:4]1[C:9]([CH2:19][CH2:20][CH3:21])([CH2:10]2)[CH2:8][CH2:7][C:6](=[O:22])[CH:5]=1.C(O)C.Cl.[OH-].[Na+].[Cl-].[NH4+:30]>C(Cl)(Cl)Cl.O>[ClH:1].[Cl:1][C:2]1[C:14]([Cl:15])=[C:13]([CH2:16][C:17](=[NH:30])[NH2:18])[CH:12]=[C:11]2[C:3]=1[C:4]1[C:9]([CH2:19][CH2:20][CH3:21])([CH2:10]2)[CH2:8][CH2:7][C:6](=[O:22])[CH:5]=1

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 702EthanolHCID 14798Sodium HydroxideHCID 25517Ammonium ChlorideHCID 14514294HCID 14514294, compound

Product 1

HCID 20040544HCID 20040544, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6212ChloroformSolvent

Procedure

(5,6-Dichloro-2,3,9,9a-tetrahydro-3-oxo-9a-propyl-1H-fluoren-7-yl)-acetonitrile (3.34 g, 10 mMole) is dissolved in chloroform (40 ml) and ethanol (650 mg, 10.9 mMole) and the mixture cooled to 0° C. The mixture is stirred and saturated with hydrogen chloride gas. After standing for 16 hours, the mixture is basified by the dropwise addition of 10 normal sodium hydroxide. The resultant chloroform solution of the imino ester free base is washed with water, dried over K2CO3 and the chloroform removed by evaporation in vacuo. The residue consisting of the imino ether is dissolved in ethanol (30 ml) and water (5 ml) then ammonium chloride (700 ml, 13 mMole) is added and the mixture stirred at room temperature for 4 hours. The mixture is filtered to remove the excess ammonium chloride and the filtrate evaporated in vacuo. Treatment with acetone gave the product which was recrystallized from a mixture of ethanol and diethyl ether.

Workup

  1. washThe resultant chloroform solution of the imino ester free base is washed with water
  2. dry with materialdried over K2CO3
  3. customthe chloroform removed by evaporation in vacuo
  4. dissolutionis dissolved in ethanol (30 ml)
  5. filtrationThe mixture is filtered
  6. customto remove the excess ammonium chloride
  7. customthe filtrate evaporated in vacuo
  8. customTreatment with acetone gave the product which
  9. customwas recrystallized from a mixture of ethanol and diethyl ether

Sources & evidence

ORD record
ord-57cd953ddfb54226b65c2f6fd573574d
Source dataset
uspto-grants-1989_05
Patent number
US04835313

Reaction notes

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