Sodium Hydroxide → HCID 22285787, compound

HRID 1061866Notes

Reaction equation

HRID 1061866 reaction equation
C([O:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]2[NH:12][C:13]3[C:18]([C:19]=2[C:20]2[CH:25]=[CH:24][C:23]([S:26]([CH3:29])(=[O:28])=[O:27])=[CH:22][CH:21]=2)=[CH:17][C:16]([Cl:30])=[CH:15][CH:14]=3)=[CH:7][CH:6]=1)(=O)C.[OH-].[Na+]>C1COCC1.C(O)C>[OH:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]2[NH:12][C:13]3[C:18]([C:19]=2[C:20]2[CH:25]=[CH:24][C:23]([S:26]([CH3:29])(=[O:27])=[O:28])=[CH:22][CH:21]=2)=[CH:17][C:16]([Cl:30])=[CH:15][CH:14]=3)=[CH:7][CH:6]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 22285774HCID 22285774, compound

Product 1

HCID 22285787HCID 22285787, compoundYield 90.7%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution 150 mg (0.34 m mol) of 2-(4-acetyloxylphenyl)-3-(4-methylsulfonylphenyl)-5-chloroindole prepared in Example 94 in 10 ml of THF was added the solution of 20 mg of NaOH in 10 ml of 95% ethanol. The reaction mixture was stirred at room temperature for 4 h, and the solvent was removed. To the residue 10 ml of 0.5N HCl was added and the resulting precipiptate was filtered off, washed with water, dried, recrystallized from 95% ethanol to afford 123 mg of the title compound as white needle crystal, yield 90.7%, m.p. 271-273° C. Analysis via Nuclear Magnetic Resonance provided the following information: 1HNMR (300 MHz, DMSO)δ:3.23 (s, 3H, SO2CH3), 6.78-7.92 (m, 11H, Ar—H), 9.78 (s, 1H, OH), 11.83 (s, 1H, N—H); Anal. Calcd for: C21H16NO3SCl: C 63.39, H 4.05, N 3.52; Found: C 63.31, H 4.24, N 3.51.

Workup

  1. customthe solvent was removed
  2. additionTo the residue 10 ml of 0.5N HCl was added
  3. filtrationthe resulting precipiptate was filtered off
  4. washwashed with water
  5. customdried
  6. customrecrystallized from 95% ethanol

Sources & evidence

ORD record
ord-1f4bfa25dfc84c3b859711c010a79bea
Source dataset
uspto-grants-2005_11
Patent number
US06960611B2

Reaction notes

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