Potassium ethylxanthate → HCID 88234431, compound

HRID 1597431Notes

Reaction equation

HRID 1597431 reaction equation
[F:1][C:2]([F:19])([F:18])[O:3][C:4]1[CH:17]=[CH:16][C:7]([O:8][C:9]2[CH:15]=[CH:14][C:12](N)=[CH:11][CH:10]=2)=[CH:6][CH:5]=1.N([O-])=O.[Na+].[CH3:24][CH2:25][O:26][C:27]([S-:29])=[S:28].[K+]>Cl.O>[C:27](=[S:28])([O:26][CH2:25][CH3:24])[S:29][C:12]1[CH:14]=[CH:15][C:9]([O:8][C:7]2[CH:16]=[CH:17][C:4]([O:3][C:2]([F:19])([F:18])[F:1])=[CH:5][CH:6]=2)=[CH:10][CH:11]=1

Participants

6

Reactant 3

HCID 2735045Potassium ethylxanthateHCID 116661924-[4-(trifluoromethoxy)phenoxy]anilineHCID 23668193Sodium Nitrite

Product 1

HCID 88234431HCID 88234431, compound

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 962WaterSolvent

Procedure

Reaction of 4-fluoro-nitrobenzene with 4-trifluoromethoxyphenol in the presence of KOtBu as described in Example 74A, followed by reduction of the nitro group (hydrogen, 10% Pd/C) gave 4-(4-trifluoromethoxyphenoxy)-aniline. The aniline (4.58 g, 17 mmol) was dissolved in conc. HCl (3.1 mL) and ice (4.5 g) cooled to −5 C., then treated with a solution of NaNO2 (1.17 g, 17 mmol) in water (7mL) which was added dropwise. The cold soltion was added to an aqueous (7 mL) solution of potassium xanthate (5.46 g, 34 mmol) and the resulting mixture was heated at 70 C for 2 h, then allowed to cool to rt and partitioned between EtOAc and water. The organic extract was dried (MgSO4), filt ered and concentrated to give the title compound

Workup

  1. additionwas added dropwise
  2. temperaturethe resulting mixture was heated at 70 C for 2 h
  3. custompartitioned between EtOAc and water
  4. extractionThe organic extract
  5. dry with materialwas dried (MgSO4)
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-a8f7d583d7224fd2a082e6da510d371d
Source dataset
uspto-grants-2001_09
Patent number
US06294573B1

Reaction notes

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