Acetonitrile → 4-Isopropyl-6-methoxy-2-saccharinylmethyl 2,4-dimethylpyridine-3 carboxylate

HRID 864762Notes

Reaction equation

HRID 864762 reaction equation
C(#N)C.C(N(CC)C(C)C)(C)C.[CH3:13][C:14]1[C:19]([C:20]([OH:22])=[O:21])=[C:18]([CH3:23])[CH:17]=[CH:16][N:15]=1.Cl[CH2:25][N:26]1[C:36](=[O:37])[C:35]2[C:30](=[CH:31][C:32]([O:41][CH3:42])=[CH:33][C:34]=2[CH:38]([CH3:40])[CH3:39])[S:27]1(=[O:29])=[O:28]>C(OCC)(=O)C>[CH3:13][C:14]1[C:19]([C:20]([O:22][CH2:25][N:26]2[C:36](=[O:37])[C:35]3[C:30](=[CH:31][C:32]([O:41][CH3:42])=[CH:33][C:34]=3[CH:38]([CH3:40])[CH3:39])[S:27]2(=[O:28])=[O:29])=[O:21])=[C:18]([CH3:23])[CH:17]=[CH:16][N:15]=1

Participants

6

Reactant 4

HCID 6342AcetonitrileHCID 81531DiisopropylethylamineHCID 15125612,4-Dimethyl-3-pyridinecarboxylic acidHCID 99951732-(Chloromethyl)-4-isopropyl-6-methoxybenzo[D]isothiazol-3(2H)-one 1,1-dioxide

Product 1

HCID 152255284-Isopropyl-6-methoxy-2-saccharinylmethyl 2,4-dimethylpyridine-3 carboxylateYield 58%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Acetonitrile (20 ml), followed by N,N-diisopropylethylamine (5.8 ml, 33 mmol) were added to 2,4-dimethyl-3-pyridinecarboxylic acid (5.1 g, 33 mmol). The mixture was stirred for 5 minutes, then 2-chloromethyl-4-isopropyl-6-methoxysaccharin (4.3 g, 14 mmol) was added. The reaction mixture was stirred at room temperature for 47 hours, then at 80° C. for 1 hour. The mixture was diluted with ethyl acetate (100 ml), washed with saturated NaHCO3, and the organic layer was dried over Na2SO4. The solvent was removed in vacuo and the residue was recrystallized from ether to afford 3,4 g (57%) of 4-isopropyl-6-methoxy-2-saccharinylmethyl 2,4-dimethylpyridine-3 carboxylate, m.p. 132.1°-133.5° C.

Workup

  1. stirringThe reaction mixture was stirred at room temperature for 47 hours
  2. waitat 80° C. for 1 hour
  3. washwashed with saturated NaHCO3
  4. dry with materialthe organic layer was dried over Na2SO4
  5. customThe solvent was removed in vacuo
  6. customthe residue was recrystallized from ether

Sources & evidence

ORD record
ord-1f34ad913fa94368a09b48677a1784a5
Source dataset
uspto-grants-1996_10
Patent number
US05563163

Reaction notes

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