Dimethylformamide → n-[4'-(2,4-Dioxothiazolidin-5-ylmethyl)-biphenyl-3-ylmethyl]-n-methylbenzamide

HRID 584892Notes

Reaction equation

HRID 584892 reaction equation
[O:1]=[C:2]1[NH:6][C:5](=[O:7])[C:4](=[CH:8][C:9]2[CH:14]=[CH:13][C:12]([C:15]3[CH:20]=[CH:19][CH:18]=[C:17]([CH2:21][N:22]([CH3:31])[C:23](=[O:30])[C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=4)[CH:16]=3)=[CH:11][CH:10]=2)[S:3]1.CN(C=O)C>C(OCC)(=O)C>[O:1]=[C:2]1[NH:6][C:5](=[O:7])[CH:4]([CH2:8][C:9]2[CH:10]=[CH:11][C:12]([C:15]3[CH:20]=[CH:19][CH:18]=[C:17]([CH2:21][N:22]([CH3:31])[C:23](=[O:30])[C:24]4[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=4)[CH:16]=3)=[CH:13][CH:14]=2)[S:3]1

Participants

4

Reactant 2

HCID 6228DimethylformamideHCID 86591247N-[4'-(2,4-dioxo-thiazolidin-5-ylidenemethyl)biphenyl-3-ylmethyl]-N-methylbenzamide

Product 1

HCID 10224631n-[4'-(2,4-Dioxothiazolidin-5-ylmethyl)-biphenyl-3-ylmethyl]-n-methylbenzamide

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

1.4 g (3.3 mmol) of N-[4′-(2,4-dioxo-thiazolidin-5-ylidenemethyl)biphenyl-3-ylmethyl]-N-methylbenzamide, 30 ml of DMF and 25 ml of ethyl acetate are introduced into a three-necked flask. The reaction medium is degassed, 1.4 g of palladium-on-charcoal (10%) are introduced and the mixture is hydrogenated under atmospheric pressure at 60° C. The reaction medium is filtered and evaporated, and the residue obtained is purified by chromatography on a column of silica eluded with a mixture of dichloromethane and methanol (99/1). After evaporation of the solvents, 300 mg (21%) of N-[4′-(2,4-dioxo-thiazolidin-5-ylmethyl)biphenyl-3-ylmethyl]-N-methylbenzamide with a melting point of 70-71° C., are collected.

Workup

  1. customThe reaction medium is degassed
  2. addition1.4 g of palladium-on-charcoal (10%) are introduced
  3. customis hydrogenated under atmospheric pressure at 60° C
  4. filtrationThe reaction medium is filtered
  5. customevaporated
  6. customthe residue obtained
  7. customis purified by chromatography on a column of silica
  8. additioneluded with a mixture of dichloromethane and methanol (99/1)
  9. customAfter evaporation of the solvents, 300 mg (21%) of N-[4′-(2,4-dioxo-thiazolidin-5-ylmethyl)biphenyl-3-ylmethyl]-N-methylbenzamide with a melting point of 70-71° C.
  10. customare collected

Sources & evidence

ORD record
ord-b91d7293b97e49dbbbdcbd0843d7a708
Source dataset
uspto-grants-2005_08
Patent number
US06927228B2

Reaction notes

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