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

HRID 338800Notes

Reaction equation

HRID 338800 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-551fb327fdb64421b6d4e36b9da88bb8
Source dataset
uspto-grants-2014_11
Patent number
US08889881B2

Reaction notes

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