Acetic Acid → HCID 67598186, compound

HRID 1417314Notes

Reaction equation

HRID 1417314 reaction equation
[NH2:1][C:2]1[CH:23]=[CH:22][C:5]([O:6][CH2:7][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:4][CH:3]=1.[N-:24]=[N+:25]=[N-:26].[Na+].[C:28](O)(=O)C>C(OC(OCC)OCC)C>[N:1]1([C:2]2[CH:3]=[CH:4][C:5]([O:6][CH2:7][CH2:8][CH2:9][CH2:10][N:11]3[C:12](=[O:21])[C:13]4[C:18](=[CH:17][CH:16]=[CH:15][CH:14]=4)[C:19]3=[O:20])=[CH:22][CH:23]=2)[CH:28]=[N:26][N:25]=[N:24]1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 33557Sodium AzideHCID 3030019HCID 3030019, compound

Product 1

HCID 67598186HCID 67598186, compound

Reagents, catalysts & solvents 1

HCID 31214Ethyl orthoformateSolvent

Procedure

To a solution of 17.7 g of 2-[4-(4-amino-phenoxy)butyl]-1H-isoindole-1,3(2H)-dione (Example 37) in a mixture of 250 ml of acetic acid and 80 ml of triethylorthoformate is added 7.0 g of sodium azide and the mixture then stirred and heated on the steam bath for 4 hours. Concentration to dryness in vacuo leaves a residue that is triturated with 250 ml of water. The insolubles are collected, washed with water, and dried. Recrystallization from ethanol gives the title compound, m.p. 143°-145° C.

Workup

  1. temperatureheated on the steam bath for 4 hours
  2. concentrationConcentration to dryness in vacuo
  3. customleaves a residue that
  4. customis triturated with 250 ml of water
  5. customThe insolubles are collected
  6. washwashed with water
  7. customdried
  8. customRecrystallization from ethanol

Sources & evidence

ORD record
ord-f4f7ca82a51541eaa0c7192f4d9af364
Source dataset
uspto-grants-1999_03
Patent number
US05877196

Reaction notes

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