Dimethylformamide → 5-[4-(2-Propyl-3-chloro-4-acetylphenoxy)butyl]-tetrazole

HRID 34972Notes

Reaction equation

HRID 34972 reaction equation
[CH2:1]([C:4]1[C:15]([Cl:16])=[C:14]([C:17](=[O:19])[CH3:18])[CH:13]=[CH:12][C:5]=1[O:6][CH2:7][CH2:8][CH2:9][C:10]#N)[CH2:2][CH3:3].[N-:20]=[N+:21]=[N-:22].[CH3:23][N:24](C)C(=[NH2+])N(C)C.CN(C)C=O.C(OCC)(=O)C>O>[CH2:1]([C:4]1[C:15]([Cl:16])=[C:14]([C:17](=[O:19])[CH3:18])[CH:13]=[CH:12][C:5]=1[O:6][CH2:7][CH2:8][CH2:9][CH2:10][C:23]1[NH:24][N:22]=[N:21][N:20]=1)[CH2:2][CH3:3]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 8857Ethyl AcetateHCID 212972634-(2-Propyl-3-chloro-4-acetylphenoxy)butane nitrileHCID 178484365HCID 178484365, compound

Product 1

HCID 1784396765-[4-(2-Propyl-3-chloro-4-acetylphenoxy)butyl]-tetrazole

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 0.5 g. of 4-(2-propyl-3- chloro-4-acetylphenoxy)butane nitrile and 1.3 g. of tetramethylguanidinium azide in 3 ml. of dimethylformamide was heated overnight at 125° C. The reaction was cooled, ethyl acetate and water were added, and the layers were separated. Water was added to the ethyl acetate layer, the water layer was acidified, and the layers were separated. The ethyl acetate was dried and evaporated to dryness. The residue was purified by chromatography to give the desired title product. NMR.

Workup

  1. temperatureThe reaction was cooled
  2. customthe layers were separated
  3. additionWater was added to the ethyl acetate layer
  4. customthe layers were separated
  5. dry with materialThe ethyl acetate was dried
  6. customevaporated to dryness
  7. customThe residue was purified by chromatography

Sources & evidence

ORD record
ord-7298b72149514b3780afca07e5e83947
Source dataset
uspto-grants-1988_08
Patent number
US04764521

Reaction notes

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