Chlorosuccinimide → HCID 54724172, compound

HRID 1867040Notes

Reaction equation

HRID 1867040 reaction equation
[OH:1][C:2]1[CH:7]=[C:6]([CH3:8])[N:5]([CH2:9][C:10]2[CH:15]=[N:14][C:13]([CH3:16])=[CH:12][N:11]=2)[C:4](=[O:17])[CH:3]=1.C1C(=O)N([Cl:25])C(=O)C1>C(O)(=O)C>[Cl:25][C:3]1[C:4](=[O:17])[N:5]([CH2:9][C:10]2[CH:15]=[N:14][C:13]([CH3:16])=[CH:12][N:11]=2)[C:6]([CH3:8])=[CH:7][C:2]=1[OH:1]

Participants

4

Reactant 2

HCID 31398ChlorosuccinimideHCID 54724183HCID 54724183, compound

Product 1

HCID 54724172HCID 54724172, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 4-hydroxy-6-methyl-1-[(5-methylpyrazin-2-yl)methyl]pyridin-2(1H)-one (1.00 g, 4.3 mmol) in glacial acetic acid (10 mL) was added NCS (0.79 g, 5.94 mmol). The reaction mixture stirred at 60° C. for 6 hours. The solvent was removed under reduced pressure and the resulting residue was triturated with ethyl acetate. The desired product was filtered and dried (0.80 g, 69%). 1H NMR (CD3OD, 400 MHz) δ 8.47 (s, 1H), 8.42 (s, 1H), 6.08 (s, 1H), 5.36 (s, 2H), 2.50 (s, 3H), 2.43 (s, 3H); ES-HRMS m/z 266.0691 (M+H calculated for C12H13N3O2Cl requires 266.0691).

Workup

  1. customThe solvent was removed under reduced pressure
  2. customthe resulting residue was triturated with ethyl acetate
  3. filtrationThe desired product was filtered
  4. customdried (0.80 g, 69%)

Sources & evidence

ORD record
ord-a77f9fd9ece046f8843a268f699cd462
Source dataset
uspto-grants-2009_12
Patent number
US07629363B2

Reaction notes

Loading…