Potassium ethylxanthate → HCID 86595994, compound

HRID 1828693Notes

Reaction equation

HRID 1828693 reaction equation
[F:1][C:2]([F:17])([F:16])[C:3]1[CH:8]=[C:7](N)[CH:6]=[CH:5][C:4]=1[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.N([O-])=O.[Na+].[K+].[CH2:23]([O:25][C:26]([S-:28])=[S:27])[CH3:24]>CO.O.Cl.CCOC(C)=O>[F:1][C:2]([F:17])([F:16])[C:3]1[CH:8]=[C:7]([S:28][C:26](=[S:27])[O:25][CH2:23][CH3:24])[CH:6]=[CH:5][C:4]=1[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

8

Reactant 3

HCID 2735045Potassium ethylxanthateHCID 16768764HCID 16768764, compoundHCID 23668193Sodium Nitrite

Product 1

HCID 86595994HCID 86595994, compound

Reagents, catalysts & solvents 4

HCID 313Hydrochloric AcidSolventHCID 887MethanolSolventHCID 962WaterSolvent3×HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

2-trifluoromethyl-biphenyl-4-ylamine (175 mg, 0.7377 mmol, 1 eq.) is dissolved in a mixture of CH3OH (0.75 mL), H2O (0.75 mL), and concentrated aqueous HCl (0.4 mL). This solution is cooled to 0° C. and a solution of NaNO2 (71 mg, 1.033 mmol, 1.4 eq.) dissolved in H2O (0.30 mL) is added slowly over 1 h, keeping the reaction temperature at 0° C. After this addition is complete, the reaction mixture is quickly added to a solution of O-ethyl-xanthic acid potassium salt (237 mg, 1.475 mmol, 2 eq.) in H2O (0.70 mL) which has been pre-heated to 65° C. This reaction mixture is stirred at 65° C. for 15 min. After cooling to room temperature, the reaction is diluted with EtOAc and washed with H2O followed by saturated aqueous NaCl. The organic solution is dried over Na2SO4. After concentration, the residue is purified by silica gel chromatography (9:1 hexanes/EtOAc) to give dithiocarbonic acid O-ethyl ester S-(2-trifluoromethyl-biphenyl-4-yl) ester.

Workup

  1. additionis added slowly over 1 h
  2. customat 0° C
  3. additionAfter this addition
  4. temperaturehas been pre-heated to 65° C
  5. temperatureAfter cooling to room temperature
  6. washwashed with H2O
  7. dry with materialThe organic solution is dried over Na2SO4
  8. concentrationAfter concentration
  9. customthe residue is purified by silica gel chromatography (9:1 hexanes/EtOAc)

Sources & evidence

ORD record
ord-a8553ed9a274424f8c05812fd9918e51
Source dataset
uspto-grants-2006_06
Patent number
US07060697B2

Reaction notes

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