Potassium Hydroxide → HCID 11582446, compound

HRID 408528Notes

Reaction equation

HRID 408528 reaction equation
Br[C:2]1[S:6][C:5]([NH:7][C:8]([C:10]2([C:13]3[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][CH:14]=3)[CH2:12][CH2:11]2)=[O:9])=[N:4][CH:3]=1.[OH-].[K+].[Cl:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=1[SH:30]>C(O)C>[Cl:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=1[S:30][C:2]1[S:6][C:5]([NH:7][C:8]([C:10]2([C:13]3[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][CH:14]=3)[CH2:12][CH2:11]2)=[O:9])=[N:4][CH:3]=1

Participants

5

Reactant 3

HCID 14797Potassium HydroxideHCID 80599o-ChlorothiophenolHCID 58609889HCID 58609889, compound

Product 1

HCID 11582446HCID 11582446, compoundYield 26%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

1-(4-Methoxy-phenyl)-cyclopropanecarboxylic acid (5-bromo-thiazol-2-yl)-amide (35 mg, 0.10 mmol) was dissolved in ethanol (0.50 mL) containing potassium hydroxide (11 mg, 0.20 mmol). 2-Chloro-benzenethiol (11 L, 0.10 mmol) is added and the mixture is subjected to microwave irradiation for 15 minutes at 115° C. The crude reaction mixture is then separated by reverse-phase preparative liquid chromatography to yield the pure product (11 mg, 0.026 mmol, 26%). ESI-MS m/z calc. 416.0. found; 417.1 (M+1)+ Retention time 4.03 minutes.

Workup

  1. customirradiation for 15 minutes at 115° C
  2. customThe crude reaction mixture
  3. customis then separated by reverse-phase preparative liquid chromatography

Sources & evidence

ORD record
ord-ebea405134c5419d84984a7f181002db
Source dataset
uspto-grants-2014_06
Patent number
US08759335B2

Reaction notes

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