4-Methylbenzoyl Chloride → N-[4'-(2,4-Dioxothiazolidin-5-ylmethyl)biphenyl-3-ylmethyl]-4,N-dimethylbenzamide

HRID 584963Notes

Reaction equation

HRID 584963 reaction equation
FC(F)(F)C(O)=O.[CH3:8][NH:9][CH2:10][C:11]1[CH:12]=[C:13]([C:17]2[CH:22]=[CH:21][C:20]([CH2:23][CH:24]3[S:28][C:27](=[O:29])[NH:26][C:25]3=[O:30])=[CH:19][CH:18]=2)[CH:14]=[CH:15][CH:16]=1.[CH3:31][C:32]1[CH:40]=[CH:39][C:35]([C:36](Cl)=[O:37])=[CH:34][CH:33]=1>>[O:29]=[C:27]1[NH:26][C:25](=[O:30])[CH:24]([CH2:23][C:20]2[CH:19]=[CH:18][C:17]([C:13]3[CH:14]=[CH:15][CH:16]=[C:11]([CH2:10][N:9]([CH3:8])[C:36](=[O:37])[C:35]4[CH:39]=[CH:40][C:32]([CH3:31])=[CH:33][CH:34]=4)[CH:12]=3)=[CH:22][CH:21]=2)[S:28]1

Participants

3

Reactant 2

HCID 134054-Methylbenzoyl ChlorideHCID 223414025-(3'-Methylaminomethylbiphenyl-4-ylmethyl)thiazolidine-2,4-dione trifluoroacetate

Product 1

HCID 10297279N-[4'-(2,4-Dioxothiazolidin-5-ylmethyl)biphenyl-3-ylmethyl]-4,N-dimethylbenzamide

Procedure

In a manner similar to that of Example 37(e), by reacting 500 mg (1.1 mmol) of 5-(3′-methylaminomethylbiphenyl-4-ylmethyl)thiazolidine-2,4-dione trifluoroacetate with 170 μl (1.25 mmol) of 4-methylbenzoyl chloride, and after purification, 350 mg (70%) of N-[4′-(2,4-dioxothiazolidin-5-ylmethyl)biphenyl-3-ylmethyl]-4, N-dimethylbenzamide are obtained in the form of a white solid with a melting point of 198° C.

Workup

  1. customafter purification, 350 mg (70%) of N-[4′-(2,4-dioxothiazolidin-5-ylmethyl)biphenyl-3-ylmethyl]-4, N-dimethylbenzamide
  2. customare obtained in the form of a white solid with a melting point of 198° C.

Sources & evidence

ORD record
ord-8b99c996262547dca120c37e7fc32df7
Source dataset
uspto-grants-2005_08
Patent number
US06927228B2

Reaction notes

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