Thionyl Chloride → HCID 19815961, compound

HRID 2247871Notes

Reaction equation

HRID 2247871 reaction equation
S(Cl)(Cl)=O.[CH3:5][C:6]1[C:11]([C:12]([OH:14])=O)=[C:10]([C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([C:21]#[N:22])[CH:16]=2)[CH:9]=[C:8]([CH3:23])[N:7]=1.[O:24]1[CH2:29][CH2:28][N:27]([CH2:30][CH2:31][NH2:32])[CH2:26][CH2:25]1.C(=O)(O)[O-].[Na+]>C(Cl)Cl.CN(C)C=O>[C:21]([C:17]1[CH:16]=[C:15]([C:10]2[CH:9]=[C:8]([CH3:23])[N:7]=[C:6]([CH3:5])[C:11]=2[C:12](=[O:14])[NH:32][CH2:31][CH2:30][N:27]2[CH2:28][CH2:29][O:24][CH2:25][CH2:26]2)[CH:20]=[CH:19][CH:18]=1)#[N:22]

Participants

7

Reactant 4

HCID 24386Thionyl ChlorideHCID 4082852-MorpholinoethylamineHCID 516892Sodium BicarbonateHCID 19815889HCID 19815889, compound

Product 1

HCID 19815961HCID 19815961, compoundYield 45.2%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent3×

Procedure

To a solution of thionyl chloride (0.29 g) in methylene chloride (5 ml) was added N,N-dimethylformamide (0.18 g) at 10° C. and the mixture was stirred at the same temperature for 1 hour. Thereto was added 2,6-dimethyl-4-(3-cyanophenyl)-3-pyridinecarboxylic acid (0.505 g) at 10° C. and the mixture was stirred at ambient temperature for 1 hour. To the resulting mixture was added dropwise a solution of 2-morpholinoethylamine (0.62 g) in methylene chloride (2 ml) at 10° C. The mixture was stirred at the same temperature for 1.5 hours, diluted with methylene chloride (10 ml) and a saturated aqueous solution of sodium bicarbonate (10 ml). The separated organic layer was washed with water and brine, dried and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (20 g) eluting with a mixture of chloroform and methanol (25:1 V/V). The fractions containing the desired compound were combined and concentrated in vacuo. The residue was tritulated with diethyl ether to give 4-(3-cyanophenyl)-2,6-dimethyl-3-(2-morpholinoethylcarbamoyl)pyridine (0.33 g).

Workup

  1. stirringthe mixture was stirred at ambient temperature for 1 hour
  2. stirringThe mixture was stirred at the same temperature for 1.5 hours
  3. washThe separated organic layer was washed with water and brine
  4. customdried
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by column chromatography on silica gel (20 g)
  7. washeluting with a mixture of chloroform and methanol (25:1 V/V)
  8. additionThe fractions containing the desired compound
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-454cdfafe56e482eb412506741675cc7
Source dataset
uspto-grants-1991_08
Patent number
US05037824

Reaction notes

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