Ammonium Chloride → HCID 70414527, compound

HRID 569305Notes

Reaction equation

HRID 569305 reaction equation
[Na].[C:2]([O:5][CH2:6][CH2:7][C:8]12[CH2:20][CH2:19][C:18](=[O:21])[CH:17]=[C:16]1[C:15]1[C:10](=[CH:11][C:12]([O:24][CH2:25][C:26]#[N:27])=[C:13]([Cl:23])[C:14]=1[Cl:22])[CH2:9]2)(=[O:4])[CH3:3].[Cl-].[NH4+:29]>CO>[ClH:22].[C:2]([O:5][CH2:6][CH2:7][C:8]12[CH2:20][CH2:19][C:18](=[O:21])[CH:17]=[C:16]1[C:15]1[C:10](=[CH:11][C:12]([O:24][CH2:25][C:26](=[NH:29])[NH2:27])=[C:13]([Cl:23])[C:14]=1[Cl:22])[CH2:9]2)(=[O:4])[CH3:3]

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 5360545SodiumHCID 20148920HCID 20148920, compound

Product 1

HCID 70414527HCID 70414527, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of sodium metal (0.116 g) in methanol (180 ml) was added {[9a-(2-acetoxyethyl)-5,6-dichloro-3-oxo-2,3,9,9a-tetrahydro-1H-fluoren-7-yl)oxy]acetonitrile (7.2 g, 18.3 mMole). The reaction mixture was stirred for 11/4 hours in a nitrogen atmosphere then treated with ammonium chloride (2.0 g, 37 mMole) and stirring was continued for 21/2 hours. The methanol was evaporated in vacuo, the residue dissolved in water, treated with 10N NaOH (10 ml), extracted with diethyl ether (100 ml) and then CH2Cl2 (3×50 ml), washed with water, dried over potassium carbonate and evaporated in vacuo. The residue was dissolved in diethyl ether, treated with a slight excess of ethanolic HCl, filtered under nitrogen, and washed with diethyl ether to give the {[9a-(2-acetoxyethyl)-5,6-dichloro-3-oxo-2,3,9,9a-tetrahydro-1H-fluoren-7-yl]oxy}ethanimidamide hydrochloride.

Workup

  1. stirringstirring
  2. custom2 hours
  3. customThe methanol was evaporated in vacuo
  4. dissolutionthe residue dissolved in water
  5. additiontreated with 10N NaOH (10 ml)
  6. extractionextracted with diethyl ether (100 ml)
  7. washCH2Cl2 (3×50 ml), washed with water
  8. dry with materialdried over potassium carbonate
  9. customevaporated in vacuo
  10. dissolutionThe residue was dissolved in diethyl ether
  11. additiontreated with a slight excess of ethanolic HCl
  12. filtrationfiltered under nitrogen
  13. washwashed with diethyl ether

Sources & evidence

ORD record
ord-bd32e1d9692f40eda5a840eae78c0780
Source dataset
uspto-grants-1988_03
Patent number
US04731471

Reaction notes

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