Sodium Hydroxide → HCID 70160832, compound

HRID 1251075Notes

Reaction equation

HRID 1251075 reaction equation
[F:1][C:2]1([F:33])[CH2:3][CH2:4][N:5](S(C2C=CC(C)=CC=2)(=O)=O)[C:6]2[CH:22]=[CH:21][CH:20]=[CH:19][C:7]=2/[C:8]/1=[CH:9]/[C:10]([N:12]1[CH2:17][CH2:16][N:15]([CH3:18])[CH2:14][CH2:13]1)=[O:11].[OH-].[Na+]>S(=O)(=O)(O)O>[F:33][C:2]1([F:1])[CH2:3][CH2:4][NH:5][C:6]2[CH:22]=[CH:21][CH:20]=[CH:19][C:7]=2/[C:8]/1=[CH:9]/[C:10]([N:12]1[CH2:13][CH2:14][N:15]([CH3:18])[CH2:16][CH2:17]1)=[O:11]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 70161439HCID 70161439, compound

Product 1

HCID 70160832HCID 70160832, compoundYield 96.4%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

(Z)-4,4-Difluoro-5-[2-(4-methylpiperazin-1-yl)-2-oxoethylidene]-1-tosyl-2,3,4,5-tetrahydro-1H-1-benzoazepine (11.7 g) was dissolved in 20 ml of concentrated sulfuric acid, followed by stirring for 24 hours at room temperature. The reaction solution was poured over 700 ml of a 1N aqueous solution of sodium hydroxide and extracted with chloroform. The organic layer was washed with a saturated aqueous solution of NaCl, and after drying over magnesium sulfate, the solvent was evaporated off. The resulting residue was crystallized from diethyl ether to give 7.62 g of (Z)-4,4-difluoro-5-[2-(4-methylpiperazin-1-yl)-2-oxoethylidene]-2,3,4,5-tetrahydro-1H-1-benzoazepine as a colorless powder.

Workup

  1. extractionextracted with chloroform
  2. washThe organic layer was washed with a saturated aqueous solution of NaCl
  3. dry with materialafter drying over magnesium sulfate
  4. customthe solvent was evaporated off
  5. customThe resulting residue was crystallized from diethyl ether

Sources & evidence

ORD record
ord-efc95f98c2d34343b53550df0de868ae
Source dataset
uspto-grants-2002_01
Patent number
US06340678B1

Reaction notes

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