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Acetic Acid → 5-(5-Chlorobenzo[d]thiazol-2-yl)benzene-1,3-diol

HRID 338791
Notes
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Reaction equation

HRID 338791 reaction equation
C(O)(=O)C.[NH2:5][C:6]1[CH:11]=[C:10]([Cl:12])[CH:9]=[CH:8][C:7]=1[SH:13].[OH:14][C:15]1[CH:16]=[C:17]([CH:20]=[C:21]([OH:23])[CH:22]=1)[CH:18]=O.C([O-])(=O)C.[Na+]>O.C(OCC)(=O)C>[Cl:12][C:10]1[CH:9]=[CH:8][C:7]2[S:13][C:18]([C:17]3[CH:20]=[C:21]([OH:23])[CH:22]=[C:15]([OH:14])[CH:16]=3)=[N:5][C:6]=2[CH:11]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 120002-Amino-4-chlorobenzenethiolHCID 943653,5-DihydroxybenzaldehydeHCID 517045Sodium Acetate

Product 1

HCID 682791185-(5-Chlorobenzo[d]thiazol-2-yl)benzene-1,3-diolYield 52.5%

Reagents, catalysts & solvents 2

HCID 962
Water
Solvent
HCID 8857Ethyl AcetateSolvent

Procedure

In an acetic acid (0.6 mL) solvent, a mixture including 2-amino-4-chlorobenzenethiol (100 mg, 0.44 mmol), 3,5-dihydroxybenzaldehyde (60 mg, 0.44 mmol), and sodium acetate (107 mg, 1.30 mmol) was refluxed for 7 hours. After cooling, the reaction mixture was distributed between ethyl acetate and water, and an organic layer was dried by using MgSO4, filtered, and evaporated under reduced pressure. The residual was purified by silica gel column chromatography using hexane and ethyl acetate (2:1) as a developer to obtain a solid Compound 90 (64.2 mg, 34.7%).

Workup

  1. temperaturewas refluxed for 7 hours
  2. temperatureAfter cooling
  3. customan organic layer was dried
  4. filtrationfiltered
  5. customevaporated under reduced pressure
  6. customThe residual was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-00de919081644ab5a0b3412e0df89b4d
Source dataset
uspto-grants-2014_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08889881B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes