Methylamine → HCID 11722609, compound

HRID 231830Notes

Reaction equation

HRID 231830 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]1[CH:18]=[N:17][CH:16]=[C:15]([CH:19]=O)[CH:14]=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:19]([C:15]3[CH:16]=[N:17][CH:18]=[CH:13][CH:14]=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

To 50 ml of toluene were added 5.0 g (0.025 mole) of α-(4-chlorophenyl)-α-mercaptoacetic acid prepared in Referential Example 4, 2.64 g (0.025 mole) of nicotinic aldehyde and 5.75 g (0.074 mole) of a 40% aqueous methylamine solution, and the mixture was subjected to azeotropic dehydration for 3 hours. The reaction mixture was cooled, and concentrated under reduced pressure. The residue obtained was purified by silica gel chromatography (5% acetone-chloroform) and recrystallized from ether to give 6.59 g (87.6% yield of 5-(4-chlorophenyl)-3-methyl-2-(3-pyridyl)-thiazolidin-4-one, m.p. 100° to 101.5° C. (uncorrected).

Workup

  1. temperatureThe reaction mixture was cooled
  2. concentrationconcentrated under reduced pressure
  3. customThe residue obtained
  4. customwas purified by silica gel chromatography (5% acetone-chloroform)
  5. customrecrystallized from ether

Sources & evidence

ORD record
ord-e8dc770bd4dd44dc8ab1f9e88ebe61ee
Source dataset
uspto-grants-1989_07
Patent number
US04849434

Reaction notes

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