Sulfuric Acid → HCID 19348329, compound

HRID 1637280Notes

Reaction equation

HRID 1637280 reaction equation
[NH2:1][CH:2]1[C:12]2[C:13]3[C:5](=[C:6]([C:15]4[CH:20]=[CH:19][C:18]([C:21]#[N:22])=[CH:17][CH:16]=4)[NH:7][C:8]=3[C:9]([Cl:14])=[CH:10][CH:11]=2)[CH2:4][CH2:3]1.S(=O)(=O)(O)[OH:24].[OH-].[Na+]>C(O)(=O)C>[NH2:1][CH:2]1[C:12]2[C:13]3[C:5](=[C:6]([C:15]4[CH:20]=[CH:19][C:18]([C:21](=[O:24])[NH2:22])=[CH:17][CH:16]=4)[NH:7][C:8]=3[C:9]([Cl:14])=[CH:10][CH:11]=2)[CH2:4][CH2:3]1

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 14798Sodium HydroxideHCID 19348360HCID 19348360, compound

Product 1

HCID 19348329HCID 19348329, compoundYield 17%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
120 °C

Procedure

A portion (1.0 g) of the compound obtained in Example 168 was dissolved in acetic acid (30 ml) and to the solution was added 50% sulfuric acid (60 ml). The mixture was stirred for 2 hours at 120° C. and allowed to cool. The reaction mixture was neutralized with 6N aqueous solution of sodium hydroxide and the insoluble matter was filtered off. The filtrate was extracted three times with ethyl acetate, washed with saturated aqueous solution of sodium chloride and dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure and the residue was crystallized from ether to yield 170 mg (17%) of the titled compound.

Workup

  1. temperatureto cool
  2. filtrationthe insoluble matter was filtered off
  3. extractionThe filtrate was extracted three times with ethyl acetate
  4. washwashed with saturated aqueous solution of sodium chloride
  5. dry with materialdried over anhydrous sodium sulfate
  6. distillationThe solvent was distilled off under reduced pressure
  7. customthe residue was crystallized from ether

Sources & evidence

ORD record
ord-2b5bdf664c0040d5a2023c8b9cd1a209
Source dataset
uspto-grants-2000_03
Patent number
US06040331

Reaction notes

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