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

HRID 1748978Notes

Reaction equation

HRID 1748978 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

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 962WaterSolventHCID 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-c89c37b647dc4c8dbc3819a8b010e7e9
Source dataset
uspto-grants-2015_10
Patent number
US09155690B2

Reaction notes

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