Sodium Hydroxide → HCID 54481653, compound

HRID 235125Notes

Reaction equation

HRID 235125 reaction equation
C([NH:9][C:10]([NH:12][C:13]1[CH:22]=[C:21]2[C:16]([CH:17]=[CH:18][CH:19]=[C:20]2[N:23]2[CH2:28][CH2:27][N:26]([CH3:29])[CH2:25][CH2:24]2)=[CH:15][CH:14]=1)=[S:11])(=O)C1C=CC=CC=1.[OH-].[Na+]>C(O)C.O>[NH2:9][C:10]([NH:12][C:13]1[CH:22]=[C:21]2[C:16]([CH:17]=[CH:18][CH:19]=[C:20]2[N:23]2[CH2:24][CH2:25][N:26]([CH3:29])[CH2:27][CH2:28]2)=[CH:15][CH:14]=1)=[S:11]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 54431880HCID 54431880, compound

Product 1

HCID 54481653HCID 54481653, compoundYield 48.1%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

The title product of example 22 (1.09 g, 2.7 mmol) was slurried in ethanol (10 mL) and a solution of 1.4 g NaOH in water (14 mL) was added. The mixture was refluxed 3 hours; then the ethanol was removed with a stream of nitrogen. The aqueous residue was extracted with methylene chloride. The organic phase was washed with brine, dried over calcium sulfate, and concentrated to leave 0.39 g (48%) of the title product. A sample was recrystallized from acetonitrile for analysis: mp 194°-195° C. Analysis calculated for C16H20N4S·CH3CN·0.5 H2O; C, 62.96; H, 6.67; N, 19.32. Found: C, 62.86; H, 6.71; N, 19.69.

Workup

  1. temperatureThe mixture was refluxed 3 hours
  2. customthen the ethanol was removed with a stream of nitrogen
  3. extractionThe aqueous residue was extracted with methylene chloride
  4. washThe organic phase was washed with brine
  5. dry with materialdried over calcium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-a45a429cfff3408d8cf3c1664a3f4e73
Source dataset
uspto-grants-1997_01
Patent number
US05597826

Reaction notes

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