Ammonia → HCID 68554795, compound

HRID 1967574Notes

Reaction equation

HRID 1967574 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([N+:22]([O-])=O)[CH:5]=[C:6]([Cl:21])[C:7]=1[O:8][C:9]1[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[C:11]([CH:17]([CH2:19][CH3:20])[CH3:18])[CH:10]=1.N>Cl.CCO.C(OCC)(=O)C>[CH:17]([C:11]1[CH:10]=[C:9]([CH:14]=[CH:13][C:12]=1[O:15][CH3:16])[O:8][C:7]1[C:6]([Cl:21])=[CH:5][C:4]([NH2:22])=[CH:3][C:2]=1[Cl:1])([CH2:19][CH3:20])[CH3:18]

Participants

6

Reactant 2

HCID 222AmmoniaHCID 25180784HCID 25180784, compound

Product 1

HCID 68554795HCID 68554795, compoundYield 100.5%

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of Stannous chloride dihydrate (194.6 g, 0.86 mol) in concentrated HCl (80.0 mL) was added to 3,5-dichloro-4-(4′-methoxy-3-sec-butyl-phenoxy)nitrobenzene (80 g, 0.21 mol) in EtOH (400 mL). The reaction mixture was refluxed for about 2 h. The resulting mixture was brought at 20-30° C. and diluted with ethyl acetate. The mixture was made alkaline with ammonia solution. Resulting solid was filtered through cellite. The organic phase was washed with H2O, brine & dried over sodium sulphate, filtered and concentrated to give 4-(3-sec-Butyl-4-methoxy-phenoxy)-3,5-dichloro-phenylamine (71.8 g; 98% yield).

Workup

  1. temperatureThe reaction mixture was refluxed for about 2 h
  2. customwas brought at 20-30° C.
  3. customResulting solid
  4. filtrationwas filtered through cellite
  5. washThe organic phase was washed with H2O, brine
  6. dry with materialdried over sodium sulphate
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-0ef994294efb4e40b5fcef05e7ef1ca0
Source dataset
uspto-grants-2013_04
Patent number
US08420851B2

Reaction notes

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