Trifluoroacetic acid → 5-[4-(1-Methylindolin-2-ylmethoxy)benzyl]thiazolidine-2,4-dione

HRID 1601762Notes

Reaction equation

HRID 1601762 reaction equation
FC(F)(F)C(O)=O.[CH3:8][N:9]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH2:11][CH:10]1[CH2:18][O:19][C:20]1[CH:52]=[CH:51][C:23]([CH2:24][CH:25]2[S:29][C:28](=[O:30])[N:27](C(C3C=CC=CC=3)(C3C=CC=CC=3)C3C=CC=CC=3)[C:26]2=[O:50])=[CH:22][CH:21]=1>C(Cl)Cl>[CH3:8][N:9]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH2:11][CH:10]1[CH2:18][O:19][C:20]1[CH:52]=[CH:51][C:23]([CH2:24][CH:25]2[S:29][C:28](=[O:30])[NH:27][C:26]2=[O:50])=[CH:22][CH:21]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 232983595-[4-(1-Methylindolin-2-ylmethoxy)benzyl]-3-triphenylmethylthiazolidine-2,4-dione

Product 1

HCID 154358525-[4-(1-Methylindolin-2-ylmethoxy)benzyl]thiazolidine-2,4-dioneYield 79.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3.1 ml of trifluoroacetic acid were added to a solution of 2.50 g of 5-[4-(1-methylindolin-2-yl-methoxy)benzyl]-3-triphenylmethylthiazolidine-2,4-dione (prepared as described in Preparation 7) in 25 ml of methylene chloride, and the resulting mixture was stirred at room temperature for 1 hour. At the end of this time, the reaction mixture was worked up following the procedure described in Example 1, to give 1.20 g of the title compound, melting at 46.1-48.9° C.

Sources & evidence

ORD record
ord-d2152390a91b45b39829ca6905d9f442
Source dataset
uspto-grants-1999_11
Patent number
US05977365

Reaction notes

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