1,3-Dichloro-2-isothiocyanatobenzene → HCID 22288834, compound

HRID 968295Notes

Reaction equation

HRID 968295 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[N:9]=[C:10]=S.[F:12][C:13]1[C:18]([F:19])=[CH:17][C:16]([NH2:20])=[C:15]([NH2:21])[CH:14]=1>C1COCC1>[ClH:1].[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[NH:9][C:10]1[NH:20][C:16]2[CH:17]=[C:18]([F:19])[C:13]([F:12])=[CH:14][C:15]=2[N:21]=1

Participants

4

Reactant 2

HCID 1232391,3-Dichloro-2-isothiocyanatobenzeneHCID 27367551,2-Diamino-4,5-difluorobenzene

Product 1

HCID 22288834HCID 22288834, compoundYield 21.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
70 °C

Procedure

2,6-Dichlorophenyl isothiocyanate (0.3 g) and 4,5-difluoro-1,2-phenylenediamine (0.21 g) were stirred at RT for 4 h in THF (15 ml) and then concentrated and dried in a high vacuum. The foamy residue was dissolved in ethanol and heated to 70° C. with stirring. Methyl iodide (0.73 ml) was then added dropwise. After three hours, the heating was stopped and the batch was allowed to stand overnight. After concentration, it was taken up using water and EA, and the EA phase was separated off, dried with magnesium sulfate, filtered, and concentrated. The residue was purified by means of preparative HPLC on RP-18 using acetonitrile/water (0.05% TFA). The clean fractions were combined, the acetonitrile was stripped off, the residue was adjusted to pH 10 with potassium carbonate solution, extracted three times with EA, and then the combined phases were dried, filtered, and concentrated. The residue was taken up using 2 N HCl and freeze-dried. 55 mg of the title compound were obtained.

Workup

  1. concentrationconcentrated
  2. customdried in a high vacuum
  3. dissolutionThe foamy residue was dissolved in ethanol
  4. additionMethyl iodide (0.73 ml) was then added dropwise
  5. waitto stand overnight
  6. concentrationAfter concentration, it
  7. customthe EA phase was separated off
  8. dry with materialdried with magnesium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated
  11. customThe residue was purified by means of preparative HPLC on RP-18 using acetonitrile/water (0.05% TFA)
  12. extractionextracted three times with EA
  13. customthe combined phases were dried
  14. filtrationfiltered
  15. concentrationconcentrated
  16. customfreeze-dried

Sources & evidence

ORD record
ord-377ddfa3c283460c83c6cdab3f8b6848
Source dataset
uspto-grants-2005_10
Patent number
US06958357B2

Reaction notes

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