Potassium Hydroxide → HCID 21957570, compound

HRID 2213542Notes

Reaction equation

HRID 2213542 reaction equation
C([O:3][C:4]([C:6]1[C:10]([CH2:11][O:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[N:9][N:8]([C:19]2[C:24]([Cl:25])=[CH:23][CH:22]=[CH:21][C:20]=2[Cl:26])[N:7]=1)=[O:5])C.[OH-].[K+]>C(O)C.O.O>[Cl:26][C:20]1[CH:21]=[CH:22][CH:23]=[C:24]([Cl:25])[C:19]=1[N:8]1[N:7]=[C:6]([C:4]([OH:5])=[O:3])[C:10]([CH2:11][O:12][C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=2)=[N:9]1

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 69652090HCID 69652090, compound

Product 1

HCID 21957570HCID 21957570, compoundYield 87.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 19096565Water ethanolSolvent

Procedure

A solution of the product from step b (1.43 g, 3.65 mmol) and potassium hydroxide (632 mg, 11.3 mmol) in ethanol/water (14 mL/2 mL) was heated at reflux for 2 h. The reaction mixture was allowed to cool and diluted with water (30 mL). The reaction mixture was washed with ether (30 mL) and the organic phase was discarded. The pH of the aqueous phase was adjusted to 1 with aqueous 2M hydrochloric acid and extracted twice with chloroform (40 mL). The combined chloroform extracts were dried (MgSO4) and the filtrate evaporated at reduced pressure to afford the title compound (1.16 g, 87%). 1H NMR (CDCl3) 7.52 (3H, m), 7.33-7.27 (2H, m), 7.08-6.99 (3H, m), 5.54 (2H, s).

Workup

  1. temperatureat reflux for 2 h
  2. temperatureto cool
  3. washThe reaction mixture was washed with ether (30 mL)
  4. extractionextracted twice with chloroform (40 mL)
  5. dry with materialThe combined chloroform extracts were dried (MgSO4)
  6. customthe filtrate evaporated at reduced pressure

Sources & evidence

ORD record
ord-01e99558d21446f2bf9c5ab08b1d2c0b
Source dataset
uspto-grants-2006_09
Patent number
US07105558B2

Reaction notes

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