Chloroform → HCID 178441991, compound

HRID 842815Notes

Reaction equation

HRID 842815 reaction equation
[CH3:1][CH:2]([CH2:7][C:8]1[CH:13]=[CH:12][C:11]([O:14][CH2:15][C:16]2[CH:21]=[CH:20][C:19]([O:22][CH2:23][C:24]3[CH:33]=[CH:32][C:31]4[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=4)[N:25]=3)=[CH:18][CH:17]=2)=[CH:10][CH:9]=1)[CH2:3][CH2:4][C:5]#[N:6].[N-:34]=[N+:35]=[N-:36].[Na+].[Cl-].[NH4+].C(Cl)(Cl)Cl>CN(C)C=O>[CH3:1][CH:2]([CH2:7][C:8]1[CH:9]=[CH:10][C:11]([O:14][CH2:15][C:16]2[CH:21]=[CH:20][C:19]([O:22][CH2:23][C:24]3[CH:33]=[CH:32][C:31]4[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=4)[N:25]=3)=[CH:18][CH:17]=2)=[CH:12][CH:13]=1)[CH2:3][CH2:4][C:5]1[NH:36][N:35]=[N:34][N:6]=1

Participants

6

Reactant 4

HCID 6212ChloroformHCID 25517Ammonium ChlorideHCID 33557Sodium AzideHCID 14774165HCID 14774165, compound

Product 1

HCID 178441991HCID 178441991, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
135 °C

Procedure

A mixture of 4-methyl-5(4-(4-(2-quinolinylmethyloxy)benzyloxy)phenyl)valeronitrile (1.5 g.), sodium azide (3 g), ammonium chloride (1.9 g) in dimethylformamide (20 ml) is stirred and heated at 135° C. for 18 hours. After cooling, the reaction mixture is poured into ice water and the insoluble material is taken up by chloroform. The residue from the evaporation of chloroform is purified by silica gel dry column (5% methanol chloroform as eluant) to yield 5-(3-methyl-4-(4-(4-(2-quinolinylmethyloxy)benzyloxy)-phenyl)butyl)tetrazole.

Workup

  1. temperatureAfter cooling
  2. customThe residue from the evaporation of chloroform
  3. customis purified by silica gel
  4. dry with materialdry column (5% methanol chloroform as eluant)

Sources & evidence

ORD record
ord-56d346cbd3634dad91a87e542c701d21
Source dataset
uspto-grants-2002_04
Patent number
US06376512B1

Reaction notes

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