Ammonium Chloride → HCID 178435847, compound

HRID 1405305Notes

Reaction equation

HRID 1405305 reaction equation
[CH2:1]([C:3]1[CH:8]=[CH:7][C:6]([C:9]2[C:18]([C:19]3[CH:24]=[CH:23][C:22]([CH2:25][CH3:26])=[CH:21][CH:20]=3)=[N:17][C:16]3[C:11](=[CH:12][CH:13]=[C:14]([C:27]#[N:28])[CH:15]=3)[N:10]=2)=[CH:5][CH:4]=1)[CH3:2].[N-:29]=[N+:30]=[N-:31].[Na+].[NH4+].[Cl-]>CN(C)C=O>[CH2:1]([C:3]1[CH:4]=[CH:5][C:6]([C:9]2[C:18]([C:19]3[CH:20]=[CH:21][C:22]([CH2:25][CH3:26])=[CH:23][CH:24]=3)=[N:17][C:16]3[C:11](=[CH:12][CH:13]=[C:14]([C:27]4[NH:31][N:30]=[N:29][N:28]=4)[CH:15]=3)[N:10]=2)=[CH:7][CH:8]=1)[CH3:2]

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 33557Sodium AzideHCID 70654351HCID 70654351, compound

Product 1

HCID 178435847HCID 178435847, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 2,3-bis(4-ethylphenyl)quinoxaline-6-carbonitrile (200 mg, 0.55 mmol, 1.00 equiv) in N,N-dimethylformamide (6 mL), NaN3 (179 mg, 2.75 mmol, 5.00 equiv), and NH4Cl (146 mg, 2.75 mmol, 5.00 equiv) was stirred for 7 h at 100° C. in an oil bath. The reaction was then quenched by the addition of water. The resulting solution was extracted with 8×50 mL of dichloromethane and the organic layers combined and dried over anhydrous sodium sulfate. The resulting solution was concentrated in vacuo, and washed with methanol. This resulted in 98 mg (44%) of 2,3-bis(4-ethylphenyl)-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 8×50 mL of dichloromethane
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationThe resulting solution was concentrated in vacuo
  5. washwashed with methanol
  6. customThis resulted in 98 mg (44%) of 2,3-bis(4-ethylphenyl)-6-(1H-tetrazol-5-yl)quinoxaline as a white solid

Sources & evidence

ORD record
ord-ee774e8e5c5840ebb8fd3984fa87bdd9
Source dataset
uspto-grants-2014_12
Patent number
US08916561B2

Reaction notes

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