Ammonium Chloride → HCID 178505541, compound

HRID 1405303Notes

Reaction equation

HRID 1405303 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:17]([C:18]3[CH:23]=[CH:22][C:21]([F:24])=[CH:20][CH:19]=3)=[N:16][C:15]3[C:10](=[CH:11][CH:12]=[C:13]([C:25]#[N:26])[CH:14]=3)[N:9]=2)=[CH:4][CH:3]=1.[N-:27]=[N+:28]=[N-:29].[Na+].[NH4+].[Cl-]>CN(C)C=O>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[C:17]([C:18]3[CH:23]=[CH:22][C:21]([F:24])=[CH:20][CH:19]=3)=[N:16][C:15]3[C:10](=[CH:11][CH:12]=[C:13]([C:25]4[NH:29][N:28]=[N:27][N:26]=4)[CH:14]=3)[N:9]=2)=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 33557Sodium AzideHCID 70654226HCID 70654226, compound

Product 1

HCID 178505541HCID 178505541, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 2,3-bis(4-fluorophenyl)quinoxaline-6-carbonitrile (150 mg, 0.44 mmol, 1.00 equiv) in N,N-dimethylformamide (10 mL), NaN3 (500 mg, 7.69 mmol, 17.59 equiv), and NH4Cl (116 mg, 2.19 mmol, 5.00 equiv) was stirred for 4 h at 100° C. in an oil bath. The reaction was then quenched by the addition of water. The resulting solution was extracted with 7×50 mL of dichloromethane and the organic layers combined and dried over anhydrous sodium sulfate. The resulting mixture was concentrated in vacuo, washed with dichloromethane, resulting in 34 mg (20%) of 2,3-bis(4-fluorophenyl)-6-(1H-tetrazol-5-yl)quinoxaline as a white solid.

Workup

  1. customThe reaction was then quenched by the addition of water
  2. extractionThe resulting solution was extracted with 7×50 mL of dichloromethane
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationThe resulting mixture was concentrated in vacuo
  5. washwashed with dichloromethane
  6. customresulting in 34 mg (20%) of 2,3-bis(4-fluorophenyl)-6-(1H-tetrazol-5-yl)quinoxaline as a white solid

Sources & evidence

ORD record
ord-7713b0f63e4f462eb5faf40e732bf71b
Source dataset
uspto-grants-2014_12
Patent number
US08916561B2

Reaction notes

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