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Hydrochloric Acid → 2-{[1-Hydroxy-4-(thiophene-2-sulfonamido)naphthalen-2-yl]sulfanyl}acetic acid

HRID 1258378
Notes
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Reaction equation

HRID 1258378 reaction equation
[OH:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([NH:12][S:13]([C:16]2[S:17][CH:18]=[CH:19][CH:20]=2)(=[O:15])=[O:14])=[CH:4][C:3]=1[S:21][CH2:22][C:23]([O:25]CC)=[O:24].Cl>O1CCOCC1.C(OCC)(=O)C>[OH:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([NH:12][S:13]([C:16]2[S:17][CH:18]=[CH:19][CH:20]=2)(=[O:15])=[O:14])=[CH:4][C:3]=1[S:21][CH2:22][C:23]([OH:25])=[O:24]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 44608823Ethyl 2-(1-hydroxy-4-(thiophene-2-sulfonamido)naphthalen-2-ylthio)acetate

Product 1

HCID 15826052-{[1-Hydroxy-4-(thiophene-2-sulfonamido)naphthalen-2-yl]sulfanyl}acetic acidYield 80.3%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 312751,4-Dioxane
Solvent

Conditions

Temperature
100 °C

Procedure

8 mg Ethyl 2-(1-hydroxy-4-(thiophene-2-sulfonamido)naphthalen-2-ylthio)acetate (9a) was dissolved in 0.5 ml dioxane, to which was added 0.5 ml HCl solution (4 N). The reaction mixture was heated at 100° C. with M.W. for 10 min and diluted to 20 ml with ethyl acetate. Washed with water and brine, the organic solution was dried over Na2SO4 and filtered. The filtrate was concentrated to dryness affording title compound 6 mg (80%) as a pale yellow solid, m.p.: 175-177° C.

Workup

  1. washWashed with water and brine
  2. dry with materialthe organic solution was dried over Na2SO4
  3. filtrationfiltered
  4. concentrationThe filtrate was concentrated to dryness

Sources & evidence

ORD record
ord-992259cb6e1748169e554fde1bd00e51
Source dataset
uspto-grants-2013_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08466157B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes