Sodium Azide → HCID 23369791, compound

HRID 1900819Notes

Reaction equation

HRID 1900819 reaction equation
I[CH2:2][C:3]1([CH3:20])[O:18][C:6]2=[C:7]3[C:12](=[C:13]([CH3:15])[CH:14]=[C:5]2[CH:4]1[CH3:19])[NH:11][C:10](=[O:16])[C:9]([CH3:17])=[CH:8]3.[N-:21]=[N+:22]=[N-:23].[Na+]>CN(C)C=O>[N:21]([CH2:2][C:3]1([CH3:20])[O:18][C:6]2=[C:7]3[C:12](=[C:13]([CH3:15])[CH:14]=[C:5]2[CH:4]1[CH3:19])[NH:11][C:10](=[O:16])[C:9]([CH3:17])=[CH:8]3)=[N+:22]=[N-:23]

Participants

4

Reactant 2

HCID 33557Sodium AzideHCID 23369684HCID 23369684, compound

Product 1

HCID 23369791HCID 23369791, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
150 °C

Procedure

To a mixture of 2-iodomethyl-2,3,5,8-tetramethyl-2,3,6,7-tetrahydrofuro[2,3-f]quinoline-7-one (1.75 g, 4.57 mmol) and sodium azide (3.5 g, 53.8 mmol), dimethylformamide (24 ml) was added, and the mixture was stirred for 3 hours in a bath at 150° C. After cooling, post-treatment and recrystallization (chloroform-n-hexane) were performed in a manner similar to that described in Example 278 to obtain 1.13 g of the title compound as pale yellow crystals (83.0%).

Workup

  1. additionwas added
  2. temperatureAfter cooling
  3. customrecrystallization (chloroform-n-hexane)

Sources & evidence

ORD record
ord-17a660dcbee244699cf8f279c6880e05
Source dataset
uspto-grants-1996_11
Patent number
US05576324

Reaction notes

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