Methanol → HCID 86591254, compound

HRID 584934Notes

Reaction equation

HRID 584934 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]([C:21]([O:23]CC)=[O:22])[CH:16]=3)=[CH:11][CH:10]=2)[S:3]1.O1CCCC1.CO.[OH-].[Na+]>O>[O:1]=[C:2]1[NH:6][C:5](=[O:7])[C:4](=[CH:8][C:9]2[CH:10]=[CH:11][C:12]([C:15]3[CH:20]=[CH:19][CH:18]=[C:17]([C:21]([OH:23])=[O:22])[CH:16]=3)=[CH:13][CH:14]=2)[S:3]1

Participants

7

Reactant 4

HCID 887MethanolHCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 91327494HCID 91327494, compound

Product 1

HCID 86591254HCID 86591254, compoundYield 94.7%

Reagents, catalysts & solvents 2

HCID 962WaterCatalystHCID 962WaterSolvent

Procedure

12.6 g (37 mmol) of ethyl 4′-(2,4-dioxo-thiazolidin-5-ylidenemethyl)biphenyl-3-carboxylate, 150 ml of tetrahydrofuran, 15 ml of methanol, a few drops of water and 7.4 g (186 mmol) of sodium hydroxide pellets are introduced into a round-bottomed flask. The mixed is refluxed for 18 hours. The reaction medium is placed in water, acidified to pH 2 and extracted with ethyl acetate. The organic phase is dried over magnesium sulfate, filtered and evaporated. 11.4 g (94%) of the desired product are obtained.

Workup

  1. temperatureThe mixed is refluxed for 18 hours
  2. extractionextracted with ethyl acetate
  3. dry with materialThe organic phase is dried over magnesium sulfate
  4. filtrationfiltered
  5. customevaporated

Sources & evidence

ORD record
ord-e3e30deba39f4896b49b265f634a8213
Source dataset
uspto-grants-2005_08
Patent number
US06927228B2

Reaction notes

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