Triethylamine → HCID 57899323, compound

HRID 425755Notes

Reaction equation

HRID 425755 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH2:9][N:10]([CH3:17])[C:11]2[CH2:15][O:14][C:13](=[O:16])[CH:12]=2)[CH:5]=[N:6][C:7]=1[Cl:8].C(N(CC)CC)C.[Cl:25]N1C(=O)CCC1=O>C(#N)C>[Cl:25][C:12]1[C:13](=[O:16])[O:14][CH2:15][C:11]=1[N:10]([CH2:9][C:4]1[CH:5]=[N:6][C:7]([Cl:8])=[C:2]([Cl:1])[CH:3]=1)[CH3:17]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31398ChlorosuccinimideHCID 16752771HCID 16752771, compound

Product 1

HCID 57899323HCID 57899323, compoundYield 84.3%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

162 mg (0.59 mmol) of 4-[[(5,6-dichloropyridin-3-yl)methyl](methyl)amino]furan-2(5H)-one (10) are dissolved in 20 ml of acetonitrile, and 90 μl (0.65 mmol) of triethylamine and 158 mg (1.19 mmol) of N-chlorosuccinimide are added at room temperature. After 1 hour of stirring, the mixture is concentrated under reduced pressure. Purification of the residue by column chromato-graphy on silica gel (silica gel 60-Merck, particle size: 0.04 to 0.063 mm) using the mobile phase mixture ethyl acetate:cyclohexane (2:1) gives 153 mg (67% of theory) of 3-chloro-4-[[(5,6-dichloropyridin-3-yl)methyl](methyl)amino]furan-2(5H)-one.

Workup

  1. concentrationthe mixture is concentrated under reduced pressure
  2. customPurification of the residue by column chromato-graphy on silica gel (silica gel 60-Merck, particle size: 0.04 to 0.063 mm)

Sources & evidence

ORD record
ord-3f9fddd5236a4c339c0989519a492c77
Source dataset
uspto-grants-2012_01
Patent number
US08106212B2

Reaction notes

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