4-Ethoxybenzoyl Chloride → N-[4'-(2,4-Dioxothiazolidin-5-ylmethyl)biphenyl-3-ylmethyl]-4-ethoxy-N-methylbenzamide

HRID 584965Notes

Reaction equation

HRID 584965 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.[CH2:31]([O:33][C:34]1[CH:42]=[CH:41][C:37]([C:38](Cl)=[O:39])=[CH:36][CH:35]=1)[CH3:32]>>[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:38](=[O:39])[C:37]4[CH:41]=[CH:42][C:34]([O:33][CH2:31][CH3:32])=[CH:35][CH:36]=4)[CH:12]=3)=[CH:22][CH:21]=2)[S:28]1

Participants

3

Reactant 2

HCID 1400594-Ethoxybenzoyl ChlorideHCID 223414025-(3'-Methylaminomethylbiphenyl-4-ylmethyl)thiazolidine-2,4-dione trifluoroacetate

Product 1

HCID 10205702N-[4'-(2,4-Dioxothiazolidin-5-ylmethyl)biphenyl-3-ylmethyl]-4-ethoxy-N-methylbenzamide

Procedure

In a manner similar to that of Example 37(e), by reacting 1 g (2.2 mmol) of 5-(3′-methylaminomethyl-biphenyl-4-ylmethyl)thiazolidine-2,4-dione trifluoro-acetate with 460 mg (2.5 mmol) of 4-ethoxybenzoyl chloride, and after purification, 960 mg (88%) of N-[4′-(2,4-dioxothiazolidin-5-ylmethyl)biphenyl-3-ylmethyl]-4-ethoxy-N-methylbenzamide are obtained in the form of a white solid with a melting point of 182° C.

Workup

  1. customafter purification, 960 mg (88%) of N-[4′-(2,4-dioxothiazolidin-5-ylmethyl)biphenyl-3-ylmethyl]-4-ethoxy-N-methylbenzamide
  2. customare obtained in the form of a white solid with a melting point of 182° C.

Sources & evidence

ORD record
ord-eba4813ab4704b3293cefa5014f4196b
Source dataset
uspto-grants-2005_08
Patent number
US06927228B2

Reaction notes

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