Ammonia → HCID 22475587, compound

HRID 2183850Notes

Reaction equation

HRID 2183850 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([N+:24]([O-:26])=[O:25])=[C:6]([CH:23]=1)[O:7][CH:8]([CH2:20][CH2:21][CH3:22])[CH2:9][CH2:10][N:11](C)[C:12](=[O:18])[O:13]C(C)(C)C.N.[C:28](=[O:31])([OH:30])[O-].[Na+]>Cl.O1CCOCC1>[C:12]([OH:18])(=[O:13])[C:28]([OH:30])=[O:31].[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([N+:24]([O-:26])=[O:25])=[C:6]([CH:23]=1)[O:7][CH:8]([CH2:20][CH2:21][CH3:22])[CH2:9][CH2:10][NH:11][CH3:12]

Participants

6

Reactant 3

HCID 222AmmoniaHCID 516892Sodium BicarbonateHCID 86587543HCID 86587543, compound

Product 1

HCID 22475587HCID 22475587, compoundYield 71%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 312751,4-DioxaneSolvent

Procedure

[3-(5-chloro-2-nitrophenoxy)hexyl]methylcarbamic acid, 1,1-dimethylethyl ester (130 mg, 0.336 mmol) was dissolved in 4M hydrogen chloride in dioxane (10 ml). The resulting solution was stirred at room temperature for 3 h, then diluted with sodium bicarbonate solution containing ammonia and extracted three times with dichloromethane. The combined organic fractions were washed with brine then dried over magnesium sulphate. The solvent was evaporated and the residue dissolved in ethanol. To this solution was added oxalic acid in ethanol and the solvent evaporated. The residue was recrystallised from ethanol to give 90 mg (71%) of the title compound as a white solid.

Workup

  1. extractionextracted three times with dichloromethane
  2. washThe combined organic fractions were washed with brine
  3. dry with materialthen dried over magnesium sulphate
  4. customThe solvent was evaporated
  5. dissolutionthe residue dissolved in ethanol
  6. additionTo this solution was added oxalic acid in ethanol
  7. customthe solvent evaporated
  8. customThe residue was recrystallised from ethanol

Sources & evidence

ORD record
ord-ac49b50cb8964b1da6bff29f49e1704e
Source dataset
uspto-grants-2005_05
Patent number
US06900243B2

Reaction notes

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