Formic Acid → 5-[(1-Ethyl-1H-benzimidazol-6-yl)methylidene]-1,3-thiazolidine-2,4-dione

HRID 2261132Notes

Reaction equation

HRID 2261132 reaction equation
[NH2:1][C:2]1[CH:15]=[CH:14][C:5]([CH:6]=[C:7]2[S:11][C:10](=[O:12])[NH:9][C:8]2=[O:13])=[CH:4][C:3]=1[NH:16][CH2:17][CH3:18].[CH:19](O)=O>>[CH2:17]([N:16]1[C:3]2[CH:4]=[C:5]([CH:6]=[C:7]3[S:11][C:10](=[O:12])[NH:9][C:8]3=[O:13])[CH:14]=[CH:15][C:2]=2[N:1]=[CH:19]1)[CH3:18]

Participants

3

Reactant 2

HCID 284Formic AcidHCID 713782715-{[4-Amino-3-(ethylamino)phenyl]methylidene}-1,3-thiazolidine-2,4-dione2×

Product 1

HCID 713782535-[(1-Ethyl-1H-benzimidazol-6-yl)methylidene]-1,3-thiazolidine-2,4-dioneYield 63%

Conditions

Temperature
100 °C

Procedure

5(4-Amino-3-ethylamino-benzylidene)-thiazolidine-2,4-dione (50 mg, 0.19 mmol) (intermediate 36) was dissolved in formic acid (5 mL) and the solution stirred at 100° C. over night. Formic acid was then removed in vacuo. The crude residue was then purified by silica gel column to give the title compound (35 mg, 63%).

Workup

  1. customFormic acid was then removed in vacuo
  2. customThe crude residue was then purified by silica gel column

Sources & evidence

ORD record
ord-06f8c6e7ee794d63a1ae3c070bed1184
Source dataset
uspto-grants-2010_12
Patent number
US07846925B2

Reaction notes

Loading…