Dimethylformamide → 5-chloro-2-[(1S)-1-{4-methyl-5-[2-(trifluoromethyl)phenyl]-4H-1,2,4-triazol-3-yl}ethoxy phenyl}-1H-tetrazole

HRID 389118Notes

Reaction equation

HRID 389118 reaction equation
[Cl-:1].[NH4+].Cl[C:4]1[CH:5]=[CH:6][C:7]([O:12][C@H:13]([C:15]2[N:19]([CH3:20])[C:18]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=3[C:27]([F:30])([F:29])[F:28])=[N:17][N:16]=2)[CH3:14])=[C:8]([CH:11]=1)C#N.[N-:31]=[N+:32]=[N-:33].[Na+].C[N:36]([CH:38]=O)C>O.C(Cl)(Cl)Cl>[Cl:1][C:38]1[NH:36][N:33]([C:8]2[CH:11]=[CH:4][CH:5]=[CH:6][C:7]=2[O:12][C@H:13]([C:15]2[N:19]([CH3:20])[C:18]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=3[C:27]([F:28])([F:30])[F:29])=[N:17][N:16]=2)[CH3:14])[NH:32][N:31]=1

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 25517Ammonium ChlorideHCID 33557Sodium AzideHCID 582439975-chloro-2-[(1S)-1-{4-methyl-5-[2-(trifluoromethyl)phenyl]-4H-1,2,4-triazol-3-yl}ethoxy}benzonitrile

Product 1

HCID 866530135-chloro-2-[(1S)-1-{4-methyl-5-[2-(trifluoromethyl)phenyl]-4H-1,2,4-triazol-3-yl}ethoxy phenyl}-1H-tetrazole

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6212ChloroformSolvent

Conditions

Temperature
100 °C

Procedure

Ammonium chloride (217 mg) was added to a mixture of 5-chloro-2-[(1S)-1-{4-methyl-5-[2-(trifluoromethyl)phenyl]-4H-1,2,4-triazol-3-yl}ethoxy}benzonitrile (330 mg), sodium azide (264 mg) and DMF (10 ml), followed by stirring at 100° C. for 16 hours. The reaction solution was added to a mixture of chloroform and water, followed by separation operation, and the organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate and then concentrated under reduced pressure. The residue was purified by silica gel column chromatography (chloroform:methanol=20:1) and the resulting product was washed with diisopropylether to obtain, as a light brown solid, 5-{5-chloro-2-[(1S)-1-{4-methyl-5-[2-(trifluoromethyl)phenyl]-4H-1,2,4-triazol-3-yl}ethoxy phenyl}-1H-tetrazole (127 mg).

Workup

  1. customfollowed by separation operation
  2. washthe organic layer was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (chloroform:methanol=20:1)
  6. washthe resulting product was washed with diisopropylether

Sources & evidence

ORD record
ord-a5e6bc5540ee48769fbd1ef2f851312b
Source dataset
uspto-grants-2013_02
Patent number
US08377923B2

Reaction notes

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