5-Bromopentanenitrile → HCID 178439672, compound

HRID 34976

Reaction equation

HRID 34976 reaction equation
[CH2:1]([C:4]1[C:10]([OH:11])=[CH:9][CH:8]=[CH:7][C:5]=1[OH:6])[CH2:2][CH3:3].Br[CH2:13][CH2:14][CH2:15][CH2:16][C:17]#[N:18].[N-:19]=[N+:20]=[N-:21].CN(C)C(=[NH2+])N(C)C>CN(C)C=O>[CH2:1]([C:4]1[C:5]([OH:6])=[CH:7][CH:8]=[CH:9][C:10]=1[O:11][CH2:13][CH2:14][CH2:15][CH2:16][C:17]1[NH:18][N:21]=[N:20][N:19]=1)[CH2:2][CH3:3]

Participants

5

Reactant 3

HCID 794355-BromopentanenitrileHCID 2620601,3-Benzenediol, propyl-HCID 178484365HCID 178484365, compound

Product 1

HCID 178439672HCID 178439672, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Six grams of 2-propylresorcinol and 6.4 g. of 5-bromovaleronitrile were reacted following cedure of Example 2A to provide 3.4 g. of the desired nitrile intermediate. This intermediate was heated to 125° C. overnight with 40 mmoles of tetramethylguanidinium azide in 10 ml. of dimethylformamide. The solvent was removed under reduced pressure and the residue was dissolved in ethyl acetate. The organic solution was washed with water adjusted to pH 6. The organic layer was dried and evaporated to yield the desired subtitle tetrazole intermediate which crystallized after evaporation of the solvent. NMR.

Workup

  1. customto provide 3.4 g
  2. customThe solvent was removed under reduced pressure
  3. dissolutionthe residue was dissolved in ethyl acetate
  4. washThe organic solution was washed with water
  5. customThe organic layer was dried
  6. customevaporated

Sources & evidence

ORD record
ord-06cd2fb2963b4f3c9f8a55e07e3e2ef8
Source dataset
uspto-grants-1988_08
Patent number
US04764521

Linked notes

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