Sodium Hydroxide → HCID 86722243, compound

HRID 869398Notes

Reaction equation

HRID 869398 reaction equation
[C:1]([C:4]1[O:5][C:6]2[CH:13]=[CH:12][C:11]([O:14][CH3:15])=[C:10]([Cl:16])[C:7]=2[C:8]=1[NH2:9])(=[O:3])[CH3:2].[CH:17]([C:19]1[N:20]=[C:21]([NH:24][C:25](=[O:29])[CH:26]([CH3:28])[CH3:27])[S:22][CH:23]=1)=O.[OH-].[Na+]>C1COCC1>[NH2:9][C:8]1[C:7]2[C:10]([Cl:16])=[C:11]([O:14][CH3:15])[CH:12]=[CH:13][C:6]=2[O:5][C:4]=1[C:1](=[O:3])[CH:2]=[CH:17][C:19]1[N:20]=[C:21]([NH:24][C:25](=[O:29])[CH:26]([CH3:27])[CH3:28])[S:22][CH:23]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 21914786HCID 21914786, compoundHCID 86722235HCID 86722235, compound

Product 1

HCID 86722243HCID 86722243, compoundYield 59.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

7G (2.5 g, 10.4 mmol) was dissolved in THF (25 mL). To the solution was added 11D (2.4 g, 1.2 eq, 12.5 mmol), followed by crushed NaOH powder (0.8 g, 2 eq, 20.8 mmol). The reaction mixture was stirred at room temperature for about 1 hour and the solution was getting darker. After reaction completed, the mixture was poured into ice-water under stirring. The solids were collected by filtration, dried and purified by column chromatography on silica gel to give 2.6 g of pure product 11E.

Workup

  1. customAfter reaction
  2. stirringunder stirring
  3. filtrationThe solids were collected by filtration
  4. customdried
  5. custompurified by column chromatography on silica gel

Sources & evidence

ORD record
ord-eb61d014c8b34da986470282e432c83f
Source dataset
uspto-grants-2015_03
Patent number
US08969373B2

Reaction notes

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