Ammonium Hydroxide → HCID 57467472, compound

HRID 1890797Notes

Reaction equation

HRID 1890797 reaction equation
[Cl:1][C:2]1[CH:14]=[CH:13][C:5]([O:6][C:7]([CH3:12])([CH3:11])[C:8](O)=[O:9])=[C:4]([F:15])[CH:3]=1.Cl.C([N:19]=C=NCCCN(C)C)C.[OH-].[NH4+]>ClCCl>[Cl:1][C:2]1[CH:14]=[CH:13][C:5]([O:6][C:7]([CH3:12])([CH3:11])[C:8]([NH2:19])=[O:9])=[C:4]([F:15])[CH:3]=1

Participants

5

Reactant 3

HCID 14923Ammonium HydroxideHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 57467471HCID 57467471, compound

Product 1

HCID 57467472HCID 57467472, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of Example 53B (14.6 g, 62.8 mmol) in dichloromethane (200 mL) was added N1-((ethylimino)methylene)-N3,N3-dimethylpropane-1,3-diamine hydrochloride (8.50 g, 55.5 mmol), and the reaction mixture was stirred for 1 hour. Ammonium hydroxide (87 mL, 628 mmol) was added. The reaction mixture was stirred at room temperature for 16 hours and then quenched with water (100 mL). The aqueous layer was extracted with dichloromethane (3×100 mL). The combined organic layers were washed with saturated NaHCO3, brine (100 mL), dried (MgSO4), filtered and concentrated. The residue was triturated with hexane/ethyl acetate (95/5) to provide the titled compound. MS (DCI+) m/z 232 (M+H)+.

Workup

  1. stirringThe reaction mixture was stirred at room temperature for 16 hours
  2. customquenched with water (100 mL)
  3. extractionThe aqueous layer was extracted with dichloromethane (3×100 mL)
  4. washThe combined organic layers were washed with saturated NaHCO3, brine (100 mL)
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was triturated with hexane/ethyl acetate (95/5)

Sources & evidence

ORD record
ord-2ac77570838d4f259599986a0b49b005
Source dataset
uspto-grants-2013_08
Patent number
US08507493B2

Reaction notes

Loading…