Hydrochloric Acid → 4-[[3,5-Bis(trimethylsilyl)benzenecarbothioyl]amino]cinnamic acid

HRID 2265112Notes

Reaction equation

HRID 2265112 reaction equation
[OH-].[Na+].[CH3:3][Si:4]([CH3:32])([CH3:31])[C:5]1[CH:6]=[C:7]([C:15]([NH:17][C:18]2[CH:30]=[CH:29][C:21]([CH:22]=[CH:23][C:24]([O:26]CC)=[O:25])=[CH:20][CH:19]=2)=[S:16])[CH:8]=[C:9]([Si:11]([CH3:14])([CH3:13])[CH3:12])[CH:10]=1.Cl>C(O)C>[CH3:14][Si:11]([CH3:12])([CH3:13])[C:9]1[CH:8]=[C:7]([C:15]([NH:17][C:18]2[CH:19]=[CH:20][C:21]([CH:22]=[CH:23][C:24]([OH:26])=[O:25])=[CH:29][CH:30]=2)=[S:16])[CH:6]=[C:5]([Si:4]([CH3:3])([CH3:31])[CH3:32])[CH:10]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 86644287Ethyl 4-[[3,5-bis(trimethylsilyl)benzenecarbothioyl]amino]cinnamate

Product 1

HCID 723015804-[[3,5-Bis(trimethylsilyl)benzenecarbothioyl]amino]cinnamic acidYield 61.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A 2N sodium hydroxide aqueous solution (6.99 ml) was added to an ethanol solution of Compound 17b (319 mg) in a nitrogen atmosphere. The obtained mixture was stirred at room temperature overnight. After the reaction was over, the reaction mixture was ice-cooled, and a 2N hydrochloric acid aqueous solution was added thereto. The precipitated solid was filtered off and recrystallized with a mixed solvent of n-hexane and ethyl acetate to obtain Compound 17 (183 mg, 61%) as a yellow solid.

Workup

  1. temperaturecooled
  2. filtrationThe precipitated solid was filtered off
  3. customrecrystallized with a mixed solvent of n-hexane and ethyl acetate

Sources & evidence

ORD record
ord-d11bb9bd4b7c425f8d64442d496d8dd3
Source dataset
uspto-grants-2010_12
Patent number
US07855300B2

Reaction notes

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