Sodium Dithionite → HCID 86665284, compound

HRID 1970844Notes

Reaction equation

HRID 1970844 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([CH3:9])[C:4]=1[NH2:10].I[C:12]([F:24])([C:17]([F:23])([F:22])[C:18]([F:21])([F:20])[F:19])[C:13]([F:16])([F:15])[F:14].S(S([O-])=O)([O-])=O.[Na+].[Na+].C(=O)([O-])O.[Na+]>O.COC(C)(C)C.S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC>[F:24][C:12]([C:7]1[CH:6]=[C:5]([CH3:9])[C:4]([NH2:10])=[C:3]([O:2][CH3:1])[CH:8]=1)([C:13]([F:14])([F:15])[F:16])[C:17]([F:22])([F:23])[C:18]([F:21])([F:20])[F:19]

Participants

8

Reactant 4

HCID 24489Sodium DithioniteHCID 4592492-Methoxy-6-methylanilineHCID 516892Sodium BicarbonateHCID 27751652-Iodoperfluorobutane

Product 1

HCID 86665284HCID 86665284, compound

Reagents, catalysts & solvents 3

HCID 94433Tetrabutylammonium hydrogen sulfateCatalystHCID 962WaterSolventHCID 15413tert-Butyl methyl etherSolvent

Procedure

To a solution of 2-methoxy-6-methylphenylamine (8.23 g, 60 mmol) in a mixture of water (60 ml) and tert-butyl methyl ether (60 ml) was added, successively 2-iodononafluorobutane (24.9 g, 11.86 ml, 72 mmol), sodium hydrosulfite (15.29 g, 72 mmol), sodium hydrogen carbonate (6.05 g, 72.0 mmol) and tetrabutyl ammonium hydrogen sulfate (“TBAHS”) (2.24 g, 6.60 mmol). The reaction mixture was stirred at ambient temperature for 16 hours. The mixture was filtered and the filtrate was extracted twice with tert-butyl methyl ether. The combined organic phases were washed with aqueous hydrochloric acid (1N), dried over sodium sulfate and concentrated to give 4-(1,2,2,3,3,3-hexafluoro-1-trifluoromethylpropyl)-2-methoxy-6-methylphenylamine which was used without further purification. LC-MS (Method 2): RT=2.05, [M+H]+=356.

Workup

  1. additionwas added
  2. filtrationThe mixture was filtered
  3. extractionthe filtrate was extracted twice with tert-butyl methyl ether
  4. washThe combined organic phases were washed with aqueous hydrochloric acid (1N)
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-0fd4a1254fa846899ab4aca769a3f260
Source dataset
uspto-grants-2013_04
Patent number
US08431514B2

Reaction notes

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