Sodium Nitrate → HCID 68528728, compound

HRID 884162Notes

Reaction equation

HRID 884162 reaction equation
N[C:2]1[CH:3]=[CH:4][C:5]([O:8][C:9]2[CH:14]=[CH:13][C:12]([C:15]([N:17]3[CH2:22][CH2:21][N:20]([CH2:23][C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=4)[CH2:19][CH2:18]3)=[O:16])=[CH:11][CH:10]=2)=[N:6][CH:7]=1.[N+]([O-])([O-])=O.[Na+].[Cl:35][C:36]1[CH:37]=[C:38]([SH:43])[CH:39]=[CH:40][C:41]=1[Cl:42]>S(=O)(=O)(O)O.O.[OH-].[Na+]>[CH2:23]([N:20]1[CH2:19][CH2:18][N:17]([C:15]([C:12]2[CH:13]=[CH:14][C:9]([O:8][C:5]3[CH:4]=[CH:3][C:2]([S:43][C:38]4[CH:39]=[CH:40][C:41]([Cl:42])=[C:36]([Cl:35])[CH:37]=4)=[CH:7][N:6]=3)=[CH:10][CH:11]=2)=[O:16])[CH2:22][CH2:21]1)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Participants

7

Reactant 3

HCID 24268Sodium NitrateHCID 799643,4-DichlorobenzenethiolHCID 68527532HCID 68527532, compound

Product 1

HCID 68528728HCID 68528728, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolvent3×HCID 1118Sulfuric AcidSolventHCID 14798Sodium HydroxideSolvent

Procedure

To a solution of [4-(5-aminopyridin-2-yloxy)phenyl](4-benzylpiperazin-1-yl)methanone (0.73 g, 1.88 mmol) in concentrated sulfuric acid (0.38 mL)-water (1.1 mL) were added dropwise a solution of sodium nitrate (0.13 g, 1.88 mmol) in water (0.6 mL) under ice cooling. The reaction mixture was stirred for 10 minutes. This reaction mixture was added to a solution of 3,4-dichlorobenzenethiol (0.24 mL, 1.88 mmol) in 2 N aqueous sodium hydroxide (2 mL) under cooling with ice. Water was added to the resulting reaction solution, and extracted with dichloromethane. The dichloromethane layer was dried over anhydrous magnesium sulfate, and evaporated. The residue was purified by silica gel chromatography (dichloromethane:methanol=80:1), to thereby yield 0.1 g of the title compound.

Workup

  1. temperatureunder cooling with ice
  2. extractionextracted with dichloromethane
  3. dry with materialThe dichloromethane layer was dried over anhydrous magnesium sulfate
  4. customevaporated
  5. customThe residue was purified by silica gel chromatography (dichloromethane:methanol=80:1)

Sources & evidence

ORD record
ord-e024806713284ab78d85e9948fcffe11
Source dataset
uspto-grants-2012_08
Patent number
US08236826B2

Reaction notes

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