Hydrochloric Acid → HCID 21278788, compound

HRID 2291546Notes

Reaction equation

HRID 2291546 reaction equation
[Cl:1][C:2]1[C:14]([Cl:15])=[C:13]([O:16][CH2:17][C:18]#[N:19])[CH:12]=[C:11]2[C:3]=1[C:4]1[C:9]([CH2:21][CH2:22][CH3:23])([C:10]2=[O:20])[CH2:8][CH2:7][C:6](=[O:24])[CH:5]=1.C(O)C.Cl.[OH-].[Na+].[Cl-].[NH4+:32]>C(Cl)(Cl)Cl>[ClH:1].[Cl:1][C:2]1[C:14]([Cl:15])=[C:13]([O:16][CH2:17][C:18](=[NH:32])[NH2:19])[CH:12]=[C:11]2[C:3]=1[C:4]1[C:9]([CH2:21][CH2:22][CH3:23])([C:10]2=[O:20])[CH2:8][CH2:7][C:6](=[O:24])[CH:5]=1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 702EthanolHCID 14798Sodium HydroxideHCID 25517Ammonium ChlorideHCID 21278783HCID 21278783, compound

Product 1

HCID 21278788HCID 21278788, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

[(5,6-Dichloro-3,9-dioxo-9a-propyl-2,3,9,9a-tetrahydro-1H-fluoren-7-yl)oxy]acetonitrile (3.49 g, 10 mMole), chloroform (40 ml) and ethanol (650 mg, 11 mMole) are united and saturated with hydrogen chloride gas at 0° C. The mixture is stirred for 16 hours and then basified with 10 normal sodium hydroxide solution. The chloroform layer is separated, washed with water, dried over K2CO3, and evaporated in vacuo. The residue is dissolved in ethanol (30 ml) and water (5 ml) added. The mixture is stirred and treated with ammonium chloride (700 mg, 12 mMole). After stirring at ambient temperature for 4 hours, the mixture is filtered, the filtrate evaporated to near dryness in vacuo, and the residue treated with acetone (50 ml). The solid that separates is removed by filtration, washed with acetone, dried, and recrystallized from a mixture of ethanol and ether to give 2-[(5,6-dichloro-3,9-dioxo-9a-propyl-2,3,9,9a-tetrahydro-1H-fluoren-7-yl)oxy]ethanimidamide hydrochloride.

Workup

  1. customThe chloroform layer is separated
  2. washwashed with water
  3. dry with materialdried over K2CO3
  4. customevaporated in vacuo
  5. dissolutionThe residue is dissolved in ethanol (30 ml)
  6. additionwater (5 ml) added
  7. stirringThe mixture is stirred
  8. stirringAfter stirring at ambient temperature for 4 hours
  9. filtrationthe mixture is filtered
  10. customthe filtrate evaporated
  11. additionthe residue treated with acetone (50 ml)
  12. customThe solid that separates is removed by filtration
  13. washwashed with acetone
  14. customdried
  15. customrecrystallized from a mixture of ethanol and ether

Sources & evidence

ORD record
ord-f18dbff2e2c24621b1e164e6bd11caf0
Source dataset
uspto-grants-1989_01
Patent number
US04797391

Reaction notes

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