Acetic Acid → 2-[4-(5-Chlorobenzo[d]thiazol-2-yl)phenoxy]-2-methylpropanoic acid

HRID 1748987Notes

Reaction equation

HRID 1748987 reaction equation
C(O)(=O)C.C([CH2:7][C:8]([O:13][C:14]1[CH:19]=[CH:18][C:17]([CH:20]=O)=[CH:16][CH:15]=1)([CH3:12])[C:9]([OH:11])=[O:10])C.[NH2:22][C:23]1[CH:28]=[C:27]([Cl:29])[CH:26]=[CH:25][C:24]=1[SH:30].C([O-])(=O)C.[Na+]>O.C(OCC)(=O)C>[Cl:29][C:27]1[CH:26]=[CH:25][C:24]2[S:30][C:20]([C:17]3[CH:16]=[CH:15][C:14]([O:13][C:8]([CH3:7])([CH3:12])[C:9]([OH:11])=[O:10])=[CH:19][CH:18]=3)=[N:22][C:23]=2[CH:28]=1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 120002-Amino-4-chlorobenzenethiolHCID 517045Sodium AcetateHCID 86709921Ethyl 2-(4-formylphenoxy)-2-methylpropanoic acid

Product 1

HCID 682793012-[4-(5-Chlorobenzo[d]thiazol-2-yl)phenoxy]-2-methylpropanoic acidYield 39.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

In an acetic acid (0.37 mL) solvent, a mixture including Compound 97c (78.2 mg, 0.38 mmol), 2-amino-4-chlorobenzenethiol (60.0 mg, 0.38 mmol), and sodium acetate (NaOAc) (93.6 mg, 1.13 mmol) was refluxed for 1 hour. After cooling, the reaction mixture was distributed between ethyl acetate and water, and an organic layer was evaporated under reduced pressure. The produced precipitate was filtered, and washed with methylene chloride to obtain Compound 99 (46.6 mg, 39.6%).

Workup

  1. temperaturewas refluxed for 1 hour
  2. temperatureAfter cooling
  3. customan organic layer was evaporated under reduced pressure
  4. filtrationThe produced precipitate was filtered
  5. washwashed with methylene chloride

Sources & evidence

ORD record
ord-9308d107df8f4d3891a4bae83295a64d
Source dataset
uspto-grants-2015_10
Patent number
US09155690B2

Reaction notes

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