Potassium Hydroxide → HCID 87182280, compound

HRID 390106Notes

Reaction equation

HRID 390106 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([C:8]2[C:16]3[C:11](=[N:12][CH:13]=[CH:14][N:15]=3)[N:10](S(C3C=CC=CC=3)(=O)=O)[CH:9]=2)[CH:5]=[C:4]([Cl:26])[N:3]=1.[OH-].[K+]>C(O)C.O>[Cl:26][C:4]1[CH:5]=[C:6]([C:8]2[C:16]3[C:11](=[N:12][CH:13]=[CH:14][N:15]=3)[NH:10][CH:9]=2)[CH:7]=[C:2]([Cl:1])[N:3]=1

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 87180537HCID 87180537, compound

Product 1

HCID 87182280HCID 87182280, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

A suspension of EXAMPLE 14A (0.300 g, 0.740 mmol) in ethanol (6 mL) was treated with a solution of potassium hydroxide (0.166 g, 2.96 mmol) in water (1.5 mL). The mixture was heated at 50° C. for 1.5 h. After cooling, the mixture was concentrated and 20% brine, sodium bicarbonate, and ethyl acetate were added. The suspension in both layers was filtered, washed with water, and dried to give the title compound. The organic layer in the filtrate was separated, dried, and concentrated. The residue was treated with ethyl acetate and diethyl ether, filtered, washed with diethyl ether, and dried to give additional title compound for a combined yield of 0.140 g (71%).

Workup

  1. temperatureAfter cooling
  2. concentrationthe mixture was concentrated
  3. addition20% brine, sodium bicarbonate, and ethyl acetate were added
  4. filtrationThe suspension in both layers was filtered
  5. washwashed with water
  6. customdried

Sources & evidence

ORD record
ord-15b3469553b5430fb442a8f690a62e24
Source dataset
uspto-grants-2013_02
Patent number
US08383624B2

Reaction notes

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