Methylamine → HCID 11722609, compound

HRID 1493237Notes

Reaction equation

HRID 1493237 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([SH:12])[C:9]([OH:11])=O)=[CH:4][CH:3]=1.[CH:13](=O)[C:14]1[CH:19]=[CH:18][CH:17]=[N:16][CH:15]=1.[CH3:21][NH2:22]>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]2[S:12][CH:13]([C:14]3[CH:15]=[N:16][CH:17]=[CH:18][CH:19]=3)[N:22]([CH3:21])[C:9]2=[O:11])=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 6329MethylamineHCID 103713-PyridinecarboxaldehydeHCID 10442855HCID 10442855, compound

Product 1

HCID 11722609HCID 11722609, compoundYield 87.6%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

α-(4-Chlorophenyl)-α-mercaptoacetic acid (5.0 g, 0.025 mol) prepared in Reference Example 4, nicotinaldehyde (2.64 g, 0.025 mol) and 40% aqueous methylamine solution (5.75 g, 0.074 mol) were added to toluene (50 ml) and the mixture was subjected to azeotropic dehydration for 3 hours. After cooled, the mixture was concentrated under reduced pressure and the residue was purified by silica gel chromatography (5% acetone-chloroform) and then recrystallized from ether to obtain 5-(4-chlorophenyl)-3-methyl-2-(3-pyridyl)-thiazolidin-4-one (6.59 g, yield 87.6%). m.p. 100°-101.5° C.

Workup

  1. temperatureAfter cooled
  2. concentrationthe mixture was concentrated under reduced pressure
  3. customthe residue was purified by silica gel chromatography (5% acetone-chloroform)
  4. customrecrystallized from ether

Sources & evidence

ORD record
ord-3ccd48d8be114e689e17fc2211bd9f99
Source dataset
uspto-grants-1991_06
Patent number
US05021435

Reaction notes

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