Hydrogen Peroxide → HCID 11524855, compound

HRID 408529Notes

Reaction equation

HRID 408529 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8][C:9]1[S:13][C:12]([NH:14][C:15]([C:17]2([C:20]3[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[CH:22][CH:21]=3)[CH2:19][CH2:18]2)=[O:16])=[N:11][CH:10]=1.OO.CC[O:32]CC.O>C(O)(=O)C>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8]([C:9]1[S:13][C:12]([NH:14][C:15]([C:17]2([C:20]3[CH:21]=[CH:22][C:23]([O:26][CH3:27])=[CH:24][CH:25]=3)[CH2:18][CH2:19]2)=[O:16])=[N:11][CH:10]=1)=[O:32]

Participants

6

Reactant 4

HCID 784Hydrogen PeroxideHCID 962WaterHCID 3283Diethyl EtherHCID 11582446HCID 11582446, compound

Product 1

HCID 11524855HCID 11524855, compoundYield 40.2%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
85 °C

Procedure

1-(4-Methoxy-phenyl)-cyclopropanecarboxylic acid [5-(2-chloro-phenylsulfanyl)-thiazol-2-yl]-amide (50.0 mg, 0.120 mmol) was dissolved in 3 mL of acetic acid containing hydrogen peroxide (30% aqueous solution, 40.8 mg, 0.360 mmol). The mixture was warmed to 85° C. for 1 hour. Ether (1.5 mL) and water (1.5 mL) was added and the layers were separated. the organic layer was dried over sodium sulfate, filtered, and evaporated to dryness. The crude reaction mixture was then separated by reverse-phase preparative liquid chromatography to yield the pure product (20.9 mg, 0.0483 mmol, 40.2%). ESI-MS m/z calc. 432.0. found; 433.3 (M+1)+ Retention time 3.34 minutes.

Workup

  1. customthe layers were separated
  2. dry with materialthe organic layer was dried over sodium sulfate
  3. filtrationfiltered
  4. customevaporated to dryness
  5. customThe crude reaction mixture
  6. customwas then separated by reverse-phase preparative liquid chromatography

Sources & evidence

ORD record
ord-10ccabc6878e4d639f7e023431d91938
Source dataset
uspto-grants-2014_06
Patent number
US08759335B2

Reaction notes

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