2,3-Dichlorophenyl Isothiocyanate → HCID 86603531, compound

HRID 2240408Notes

Reaction equation

HRID 2240408 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[C:14]([CH2:15][NH2:16])=[CH:13][CH:12]=[CH:11][N:10]=1.[Cl:17][C:18]1[C:23]([Cl:24])=[CH:22][CH:21]=[CH:20][C:19]=1[N:25]=[C:26]=[S:27]>C(=O)(O)[O-].[Na+]>[Cl:17][C:18]1[C:23]([Cl:24])=[CH:22][CH:21]=[CH:20][C:19]=1[NH:25][C:26]([NH:16][CH2:15][C:14]1[C:9]([C:4]2[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=2[O:2][CH3:1])=[N:10][CH:11]=[CH:12][CH:13]=1)=[S:27]

Participants

4

Reactant 2

HCID 27962812,3-Dichlorophenyl IsothiocyanateHCID 68583564HCID 68583564, compound

Product 1

HCID 86603531HCID 86603531, compoundYield 85.1%

Reagents, catalysts & solvents 1

HCID 516892Sodium BicarbonateSolvent

Procedure

To an oven-dried, N2-purged, 25-mL, round-bottomed flask containing a magnetic stir bar was added the crude C-[2-(2-methoxy-phenyl)-pyridin-3-yl]-methylamine (430 mg, 2.0 mmol) from above. The flask was sealed with a septum and purged with N2 atmosphere. Anhydrous tetrahydrofuran (10 mL) was added via syringe. Neat 2,3-dichlorophenylisothiocyanate (510 mg, 356 μL, 2.50 mmol) was added via syringe. The pale green solution was stirred at room temperature overnight. Saturated aqueous sodium bicarbonate (10 mL) was added to quench. The mixture was transferred to a separatory funnel and extracted with dichloromethane (3×10 mL). The combined organic extracts were dried over magnesium sulfate, filtered, and concentrated by rotary evaporator to give a tan solid. The product was recrystallized from ethyl acetate/hexanes to give a 712 mg (85%) of the title compound as a white powder. MS (LC-MS, ESI+) m/z 417.0 (M+H)+; 1H NMR (DMSO-d6) δ 3.74 (s, 3H), 4.35 (br s, 1H), 4.66 (br s, 1H), 7.03-7.13 (m, 2H), 7.22 (dd, J=7.5, 1.7 Hz, 1H), 7.31-7.60 (m, 6H), 7.74 (dd, J=7.1, 1.0 Hz, 1H), 8.23 (br s, 1H), 8.51 (dd, J=4.9, 1.5 Hz, 1H), 9.46 (br s, 1H).

Workup

  1. customTo an oven-dried, N2-purged
  2. addition25-mL, round-bottomed flask containing a magnetic stir bar
  3. customThe flask was sealed with a septum
  4. custompurged with N2 atmosphere
  5. additionAnhydrous tetrahydrofuran (10 mL) was added via syringe
  6. customto quench
  7. customThe mixture was transferred to a separatory funnel
  8. extractionextracted with dichloromethane (3×10 mL)
  9. dry with materialThe combined organic extracts were dried over magnesium sulfate
  10. filtrationfiltered
  11. concentrationconcentrated by rotary evaporator
  12. customto give a tan solid
  13. customThe product was recrystallized from ethyl acetate/hexanes

Sources & evidence

ORD record
ord-5d9b61a8d9d44c14a23c4f1fed52c294
Source dataset
uspto-grants-2010_05
Patent number
US07723367B2

Reaction notes

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