2,3-Dichlorophenyl Isothiocyanate → HCID 86603531, compound

HRID 1512311Notes

Reaction equation

HRID 1512311 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-738fc16d7dce40e395948417479bfbca
Source dataset
uspto-grants-2012_07
Patent number
US08217067B2

Reaction notes

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