Hydrochloric Acid → 5-(4-Hydroxy-phenylsulfanyl)-4-nitro-thiophene-2-carboxylic acid

HRID 605312Notes

Reaction equation

HRID 605312 reaction equation
C([O:3][C:4]([C:6]1[S:7][C:8]([S:14][C:15]2[CH:20]=[CH:19][C:18]([OH:21])=[CH:17][CH:16]=2)=[C:9]([N+:11]([O-:13])=[O:12])[CH:10]=1)=[O:5])C.[OH-].[Li+].Cl>CO.O>[OH:21][C:18]1[CH:17]=[CH:16][C:15]([S:14][C:8]2[S:7][C:6]([C:4]([OH:5])=[O:3])=[CH:10][C:9]=2[N+:11]([O-:13])=[O:12])=[CH:20][CH:19]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 67040477HCID 67040477, compound

Product 1

HCID 670406395-(4-Hydroxy-phenylsulfanyl)-4-nitro-thiophene-2-carboxylic acid

Reagents, catalysts & solvents 1

HCID 22242641Methanol--water (1/1)Solvent

Procedure

The product from Example 351B (1 equiv) was dissolved in a methanol/water 3/1 mixture followed by the addition of lithium hydroxide (5 equiv). The resultant solution was stirred at room temperature for 24 hours followed by the addition of 1N aqueous hydrochloric acid until the solution was a pH of 2. The mixture was then extracted with ethyl acetate, the organic extracts dried and concentrated under vacuum to provide the title product.

Workup

  1. extractionThe mixture was then extracted with ethyl acetate
  2. customthe organic extracts dried
  3. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-20d042b3277e432e91741c483436e6ed
Source dataset
uspto-grants-2011_03
Patent number
US07910595B2

Reaction notes

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