Sodium Azide → HCID 178437413, compound

HRID 1199709Notes

Reaction equation

HRID 1199709 reaction equation
[N-:1]=[N+:2]=[N-:3].[Na+].[C:5]([CH2:7][CH2:8][CH2:9][NH:10][C:11]1[CH:12]=[C:13]([CH:25]=[CH:26][CH:27]=1)/[CH:14]=[CH:15]/[C:16]1[S:17][C:18]2[CH:24]=[CH:23][CH:22]=[CH:21][C:19]=2[N:20]=1)#[N:6]>CN(C)C=O>[NH:1]1[C:5]([CH2:7][CH2:8][CH2:9][NH:10][C:11]2[CH:12]=[C:13]([CH:25]=[CH:26][CH:27]=2)/[CH:14]=[CH:15]/[C:16]2[S:17][C:18]3[CH:24]=[CH:23][CH:22]=[CH:21][C:19]=3[N:20]=2)=[N:6][N:3]=[N:2]1

Participants

4

Reactant 2

HCID 33557Sodium AzideHCID 14051164HCID 14051164, compound

Product 1

HCID 178437413HCID 178437413, compoundYield 35%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
120 °C

Procedure

To 5 ml of dimethylformamide were added 390 mg of sodium azide and 638 mg of 2-[trans-3-(3-cyanopropylamino)styryl]benzothiazole, and the mixture was heated to 120° C. for 7 hours. After cooled to room temperature, the mixture was extracted with ethyl acetate, dried over anhydrous magnesium sulfate and the solvent was evaporation under reduced pressure. The concentrate was purified through silica gel column chromatography by use of ethyl acetate to obtain 250 mg (yield 35%) of the title compound.

Workup

  1. temperatureAfter cooled to room temperature
  2. extractionthe mixture was extracted with ethyl acetate
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customevaporation under reduced pressure
  5. customThe concentrate was purified through silica gel column chromatography by use of ethyl acetate

Sources & evidence

ORD record
ord-ed8033e821d84588a6a2bcfff40c3b30
Source dataset
uspto-grants-1990_02
Patent number
US04902700

Reaction notes

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