Dimethylformamide → HCID 178514903, compound

HRID 894184Notes

Reaction equation

HRID 894184 reaction equation
[O:1]=[C:2]1[C:8]2[CH:9]=[C:10]([C:13]#[N:14])[CH:11]=[CH:12][C:7]=2[CH2:6][O:5][C:4]2[CH:15]=[CH:16][CH:17]=[CH:18][C:3]1=2.[N-:19]=[N+:20]=[N-:21].[Na+].[Cl-].[NH4+].CN(C)C=O>O.C(=O)([O-])[O-].[Na+].[Na+]>[NH:19]1[C:13]([C:10]2[CH:11]=[CH:12][C:7]3[CH2:6][O:5][C:4]4[CH:15]=[CH:16][CH:17]=[CH:18][C:3]=4[C:2](=[O:1])[C:8]=3[CH:9]=2)=[N:14][N:21]=[N:20]1

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 25517Ammonium ChlorideHCID 33557Sodium AzideHCID 129291409-Cyano-6,11-dihydro-11-oxodibenz[b,e]oxepin

Product 1

HCID 178514903HCID 178514903, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 10340Sodium CarbonateSolvent

Procedure

Heat a mixture of 800 mg. of the nitrile of Example 2, Step F, 293 mg. of sodium azide and 265 mg. of ammonium chloride in 25 ml. of dimethylformamide at 130°-135° C. for 6 hours. Dilute the mixture with water and excess sodium carbonate. Extract with ethyl acetate. Acidify the aqueous phase and separate and precipitate by filtration to obtain the title product.

Workup

  1. temperatureHeat
  2. additiona mixture of 800 mg
  3. extractionExtract with ethyl acetate
  4. customseparate
  5. filtrationprecipitate by filtration

Sources & evidence

ORD record
ord-dcbf31fad5c046beac63d224d1423e91
Source dataset
uspto-grants-1981_08
Patent number
US04282365

Reaction notes

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