Phenylacetyl chloride → n-[4'-(2,4-Dioxothiazolidin-5-ylidenemethyl)-biphenyl-3-yl]-n-methyl-2-phenylacetamide

HRID 584982Notes

Reaction equation

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

Participants

Reactant 2

HCID 7679Phenylacetyl chloride

HCID 865989415-(3'-Methylaminobiphenyl-4-ylmethylene)thiazolidine-2,4-dione

Product 1

HCID 131725064n-[4'-(2,4-Dioxothiazolidin-5-ylidenemethyl)-biphenyl-3-yl]-n-methyl-2-phenylacetamide

Procedure

In a manner similar to that of Example 37(e), by reacting 1 g (3.2 mmol) of 5-(3′-methylaminobiphenyl-4-ylmethylene)thiazolidine-2,4,dione with 470 μl (3.5 mmol) of phenylacetyl chloride, and after purification, 1.4 g (50%) of N-[4′-(2,4-dioxothiazolidin-5-ylidenemethyl)biphenyl-3-yl]-N-methyl-2-phenylacetamide are obtained.

Workup

customafter purification, 1.4 g (50%) of N-[4′-(2,4-dioxothiazolidin-5-ylidenemethyl)biphenyl-3-yl]-N-methyl-2-phenylacetamide
customare obtained

Sources & evidence

ORD record: ord-1c4e48c895ad4df598ce41c7ce8919cf
Source dataset: uspto-grants-2005_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06927228B2

Reaction notes

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