Pyridine → HCID 67693570, compound

HRID 1417335Notes

Reaction equation

HRID 1417335 reaction equation
Cl.[NH2:2][C:3]1[CH:23]=[CH:22][C:6]([O:7][CH2:8][CH2:9][CH2:10][N:11]2[C:19](=[O:20])[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[C:12]2=[O:21])=[CH:5][CH:4]=1.N1C=CC=CC=1.[OH-].[Na+].[CH3:32][S:33](Cl)(=[O:35])=[O:34]>O>[O:20]=[C:19]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[C:12](=[O:21])[N:11]1[CH2:10][CH2:9][CH2:8][O:7][C:6]1[CH:22]=[CH:23][C:3]([NH:2][S:33]([CH3:32])(=[O:35])=[O:34])=[CH:4][CH:5]=1

Participants

6

Reactant 4

HCID 1049PyridineHCID 14798Sodium HydroxideHCID 31297Methanesulfonyl chlorideHCID 67598410HCID 67598410, compound

Product 1

HCID 67693570HCID 67693570, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A 7.0 g sample of 2-[3-(4-aminophenoxy)-propyl]-1H-isoindole-1,3(2H)-dione monohydrochloride (Example 95) is added to 100 ml of pyridine, 2.2 ml of 10N NaOH and 2.5 g methanesulfonyl chloride. The mixture is stirred at room temperature for 6 hours and 1 hour on a steam bath. The reaction mixture is poured into 900 ml of cold water and stored at 0° C. for 18 hours. The precipitate is collected, washed with 200 ml of water and dried to give 6.5 g of solid. A 1.0 g sample is crystallized from 100 ml of boiling ethanol after treatment with activated carbon to give 0.6 g of solid, m.p. 176°-178° C.

Workup

  1. waitstored at 0° C. for 18 hours
  2. customThe precipitate is collected
  3. washwashed with 200 ml of water
  4. customdried

Sources & evidence

ORD record
ord-8a74ea33a4734084876db9809afc97c0
Source dataset
uspto-grants-1999_03
Patent number
US05877196

Reaction notes

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