HCID 73455757, compound → HCID 18668954, compound

HRID 1058667Notes

Reaction equation

HRID 1058667 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:21]=[CH:22][C:23]=1[Cl:24])[CH2:5][S:6][C:7]1[N:12]=[C:11]([CH:13]=[C:14]2[S:18][C:17](=[S:19])[NH:16][C:15]2=[O:20])[CH:10]=[CH:9][N:8]=1>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:3]=[C:4]([CH:21]=[CH:22][C:23]=1[Cl:24])[CH2:5][S:6][C:7]1[N:12]=[C:11]([CH2:13][CH:14]2[S:18][C:17](=[S:19])[NH:16][C:15]2=[O:20])[CH:10]=[CH:9][N:8]=1

Participants

3

Reactant 1

HCID 73455757HCID 73455757, compound

Product 1

HCID 18668954HCID 18668954, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A suspension of 5-[2-(3,4-dichloro-benzylsulfanyl)-pyrimidin-4-ylmethylene]-2-thioxo-thiazolidin-4-one in toluene was heated to 80° C. in the presence of 2,6-dimethyl-1,4-dihydro-3,5-pyridine carboxylate (1.1 eq.) and activated silica gel. The suspension was filtered and rinsed with EtOAc. The filtrate was evaporated in vacuum and the resulting residue was redissolved in EtOAc and washed with 1N aq. HCl solution. The organic layer was dried over Na2SO4 and concentrated under vacuum to give the crude product. Flash chromatography afforded pure product.

Workup

  1. filtrationThe suspension was filtered
  2. washrinsed with EtOAc
  3. customThe filtrate was evaporated in vacuum
  4. dissolutionthe resulting residue was redissolved in EtOAc
  5. washwashed with 1N aq. HCl solution
  6. dry with materialThe organic layer was dried over Na2SO4
  7. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-eeebe174484e4a9a965eb1d71c643947
Source dataset
uspto-grants-2003_02
Patent number
US06518268B1

Reaction notes

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