Sodium Azide → HCID 54206894, compound

HRID 1863085Notes

Reaction equation

HRID 1863085 reaction equation
Cl[CH2:2][CH2:3][CH2:4][NH:5][C:6]([C:8]1[N:9]([CH3:24])[C:10]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[C:11]2[C:16]=1[CH:15]=[CH:14][C:13]([Cl:17])=[CH:12]2)=[O:7].[N-:25]=[N+:26]=[N-:27].[Na+]>CN(C)C=O>[N:25]([CH2:2][CH2:3][CH2:4][NH:5][C:6]([C:8]1[N:9]([CH3:24])[C:10]([C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=2)=[C:11]2[C:16]=1[CH:15]=[CH:14][C:13]([Cl:17])=[CH:12]2)=[O:7])=[N+:26]=[N-:27]

Participants

4

Reactant 2

HCID 33557Sodium AzideHCID 53957864HCID 53957864, compound

Product 1

HCID 54206894HCID 54206894, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A suspension of 14.4 g. of 5-chloro-2-methyl-3-phenylisoindole-1-carboxylic acid (3-chloropropyl)amide in 80 ml. of dimethylformamide is treated with 5.2 g. of sodium azide and the mixture is stirred at 60° C. for 4 hours. The mixture is cooled and poured on to 500 ml. of ice-water. The separated product is removed by filtration under suction, washed with water and dissolved in methylene chloride. The organic solution is washed with a saturated aqueous sodium chloride solution, dried over sodium sulfate and evaporated. The solid residue is triturated with a small amount of ether and filtered, whereby there is obtained 5-chloro-2-methyl-3-phenylisoindole-1-carboxylic acid (3-azidopropyl)amide having a melting point of 143°-146° C. (decomposition) which can be used in the process without further purification. An analytical sample is obtained by recrystallization from methanol and has a melting point of 148°-150° C. (decomposition).

Workup

  1. additionA suspension of 14.4 g
  2. temperatureThe mixture is cooled
  3. additionpoured on to 500 ml
  4. customThe separated product is removed by filtration under suction
  5. washwashed with water
  6. dissolutiondissolved in methylene chloride
  7. washThe organic solution is washed with a saturated aqueous sodium chloride solution
  8. dry with materialdried over sodium sulfate
  9. customevaporated
  10. customThe solid residue is triturated with a small amount of ether
  11. filtrationfiltered

Sources & evidence

ORD record
ord-f63f57cb71c1413786fe4025448e34f0
Source dataset
uspto-grants-1979_09
Patent number
US04167632

Reaction notes

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