Benzoyl isothiocyanate → HCID 59603087, compound

HRID 2068710Notes

Reaction equation

HRID 2068710 reaction equation
[NH2:1][C:2]1[C:3]([F:9])=[N:4][CH:5]=[C:6]([Br:8])[CH:7]=1.[C:10]([N:18]=[C:19]=[S:20])(=[O:17])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1>CC(C)=O>[Br:8][C:6]1[CH:7]=[C:2]([NH:1][C:19]([NH:18][C:10](=[O:17])[C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=2)=[S:20])[C:3]([F:9])=[N:4][CH:5]=1

Participants

4

Reactant 2

HCID 68284Benzoyl isothiocyanateHCID 177501445-Bromo-2-fluoropyridin-3-amine

Product 1

HCID 59603087HCID 59603087, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent2×

Procedure

To a solution of 3-amino-5-bromo-2-fluoropyridine (1.0 g, 5.23 mmol) in acetone (15.0 mL) was added benzoylisothiocyanate (0.85 mL, 6.25 mmol) and the resulting reaction mixture was stirred at room temperature for 30 min. After the completion of the reaction (TLC monitoring), acetone was removed under reduced pressure and the residue was washed with hexane and filtered to obtain the desired product (1.68 g, 91%). 1H NMR (400 MHz, DMSO-d6): δ 7.55 (t, J=7.60 Hz, 2H), 7.68 (t, J=7.60 Hz, 1H), 8.0 (d, J=7.60 Hz, 2H), 8.31 (s, 1H), 8.84 (dd, J=2.0 and 8.40 Hz, 1H), 12.03 (br s, 1H) and 12.60 (br s, 1H).

Workup

  1. customthe resulting reaction mixture
  2. customwas removed under reduced pressure
  3. washthe residue was washed with hexane
  4. filtrationfiltered

Sources & evidence

ORD record
ord-80662c98a7f1417496d1da1fc35f1825
Source dataset
uspto-grants-2012_10
Patent number
US08299065B2

Reaction notes

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