3,5-Dichlorobenzoyl chloride → 3,5-Dichloro-N-[4'-(2,4-dioxothiazolidin-5-ylmethyl)biphenyl-3-ylmethyl]-N-methylbenzamide

HRID 584969Notes

Reaction equation

HRID 584969 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.[Cl:31][C:32]1[CH:33]=[C:34]([CH:38]=[C:39]([Cl:41])[CH:40]=1)[C:35](Cl)=[O:36]>>[Cl:31][C:32]1[CH:33]=[C:34]([CH:38]=[C:39]([Cl:41])[CH:40]=1)[C:35]([N:9]([CH2:10][C:11]1[CH:12]=[C:13]([C:17]2[CH:18]=[CH:19][C:20]([CH2:23][CH:24]3[S:28][C:27](=[O:29])[NH:26][C:25]3=[O:30])=[CH:21][CH:22]=2)[CH:14]=[CH:15][CH:16]=1)[CH3:8])=[O:36]

Participants

3

Reactant 2

HCID 761913,5-Dichlorobenzoyl chlorideHCID 223414025-(3'-Methylaminomethylbiphenyl-4-ylmethyl)thiazolidine-2,4-dione trifluoroacetate

Product 1

HCID 102071203,5-Dichloro-N-[4'-(2,4-dioxothiazolidin-5-ylmethyl)biphenyl-3-ylmethyl]-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 350 μl (2.5 mmol) of 3,5-dichlorobenzoyl chloride, and after purification, 400 mg (50%) of 3,5-dichloro-N-[4′-(2,4-dioxothiazolidin-5-ylmethyl)-biphenyl-3-ylmethyl]-N-methylbenzamide are obtained in the form of a white solid with a melting point of 106° C.

Workup

  1. customafter purification, 400 mg (50%) of 3,5-dichloro-N-[4′-(2,4-dioxothiazolidin-5-ylmethyl)-biphenyl-3-ylmethyl]-N-methylbenzamide
  2. customare obtained in the form of a white solid with a melting point of 106° C.

Sources & evidence

ORD record
ord-ac2d7e1ca2bc4e898308dc5602a14bf5
Source dataset
uspto-grants-2005_08
Patent number
US06927228B2

Reaction notes

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