Bicarbonate Ion → 5-(3'-Methylaminomethylbiphenyl-4-ylidene-methyl) thiazolidine-2,4-dione

HRID 584907Notes

Reaction equation

HRID 584907 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](C)[C:23](=O)OC(C)(C)C)[CH:16]=3)=[CH:11][CH:10]=2)[S:3]1.FC(F)(F)C(O)=O.C(=O)(O)[O-]>ClCCl>[CH3:23][NH:22][CH2:21][C:17]1[CH:16]=[C:15]([C:12]2[CH:11]=[CH:10][C:9](=[CH:8][CH:4]3[S:3][C:2](=[O:1])[NH:6][C:5]3=[O:7])[CH2:14][CH:13]=2)[CH:20]=[CH:19][CH:18]=1

Participants

5

Reactant 3

HCID 769Bicarbonate IonHCID 6422Trifluoroacetic acidHCID 86598938Tert-butyl [4'-(2,4-dioxothiazolidin-5-ylidenemethyl)biphenyl-3-ylmethyl]methylcarbamate

Product 1

HCID 879537375-(3'-Methylaminomethylbiphenyl-4-ylidene-methyl) thiazolidine-2,4-dioneYield 85%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2 g (4.7 mmol) of tert-butyl [4′-(2,4-dioxo-thiazolidin-5-ylidenemethyl)biphenyl-3-ylmethyl]methyl-carbamate and 20 ml of dichloromethane are introduced into a round-bottomed flask. 2.2 ml (28.2 mmol) of trifluoroacetic acid are added and the mixture is stirred at room temperature for four hours. The reaction medium is poured into aqueous bicarbonate solution and extracted with dichloromethane, and the organic phase is separated out after settling of the phases has taken place, dried over magnesium sulfate and evaporated. 1.3 g (85%) of the expected product are obtained.

Workup

  1. extractionextracted with dichloromethane
  2. customthe organic phase is separated out
  3. dry with materialdried over magnesium sulfate
  4. customevaporated

Sources & evidence

ORD record
ord-bd6b0e114bed4dbd92d791439bf58253
Source dataset
uspto-grants-2005_08
Patent number
US06927228B2

Reaction notes

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