Sodium Hydroxide → HCID 67532800, compound

HRID 1713071Notes

Reaction equation

HRID 1713071 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([CH:28]=[CH:29][CH:30]=1)[C:5]([C:7]1[C:15]2[CH:14]=[CH:13][C:12](=[O:16])[N:11]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[C:10]=2[S:9][C:8]=1[C:23]([O:25]CC)=[O:24])=[O:6].[OH-].[Na+]>CCO>[CH3:1][C:2]1[CH:3]=[C:4]([CH:28]=[CH:29][CH:30]=1)[C:5]([C:7]1[C:15]2[CH:14]=[CH:13][C:12](=[O:16])[N:11]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[C:10]=2[S:9][C:8]=1[C:23]([OH:25])=[O:24])=[O:6]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 11395960HCID 11395960, compound

Product 1

HCID 67532800HCID 67532800, compoundYield 81.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of Example 1 (4.23 g, 10 mmol) and 0.25M NaOH(aq) (48 ml, 12 mmol) in EtOH (100 ml) was heated at reflux for 1 h. The solution was cooled to r.t. and the solvent removed in vacuo. The residue was dissolved in water (ca. 10 ml) and poured into 2M HCl(aq) (200 ml). The precipitate was filtered and dried in vacuo to give the title compound as a white solid (3.17 g, 81%). δH (DMSO-d6) 7.64-7.53 (7H, m), 7.48-7.43 (2H, m), 7.39 (1H, t, J 7.6 Hz), 6.49 (1H, d, J 9.6 Hz), 2.32 (3H, s). LCMS (ES+) RT 3.19 minutes, 390 (M+H)+.

Workup

  1. temperatureat reflux for 1 h
  2. customthe solvent removed in vacuo
  3. dissolutionThe residue was dissolved in water (ca. 10 ml)
  4. additionpoured into 2M HCl(aq) (200 ml)
  5. filtrationThe precipitate was filtered
  6. customdried in vacuo

Sources & evidence

ORD record
ord-cd9e14dc12934302bb7a23b4f3b1944f
Source dataset
uspto-grants-2010_09
Patent number
US07795256B2

Reaction notes

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