Diethyl Ether → HCID 73444541, compound

HRID 1281141Notes

Reaction equation

HRID 1281141 reaction equation
[CH:1]([C:3]1[CH:16]=[CH:15][C:6]([CH:7]=[C:8]2[S:12][C:11](=[O:13])[NH:10][C:9]2=[O:14])=[CH:5][CH:4]=1)=O.[NH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1[SH:24].C1(=O)C=CC(=O)C=C1.CCOCC>C(O)C>[O:13]=[C:11]1[NH:10][C:9](=[O:14])[C:8](=[CH:7][C:6]2[CH:15]=[CH:16][C:3]([C:1]3[S:24][C:19]4[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=4[N:17]=3)=[CH:4][CH:5]=2)[S:12]1

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 4650QuinoneHCID 87132-AminothiophenolHCID 32727725-(4-Formylbenzylidene)-2,4-thiazolidinedione

Product 1

HCID 73444541HCID 73444541, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a suspension of 5-(4-formylbenzylidene)-2,4-thiazolidinedione (50 mg, 0.21 mmol) and 2-aminothiophenol (0.025 mL, 0.23 mmol) in ethanol (7 mL) was heated to reflux for 10 h. 1,4-Benzoquinone (24 mg, 0.22 mmol) was added, and the mixture was heated additional 1 h. The mixture was cooled to room temperature, ether (3 mL) was added, and the precipitated product was collected by filtration to afford 2-[4-(2,4-dioxothiazolidin-5-ylidenemethyl)phenyl]benzothiazole (53 mg, 75%).

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 10 h
  3. temperaturethe mixture was heated additional 1 h
  4. filtrationthe precipitated product was collected by filtration

Sources & evidence

ORD record
ord-abea2439b86f4017b39972f09823200c
Source dataset
uspto-grants-2002_09
Patent number
US06452014B1

Reaction notes

Loading…