Tetrahydrofuran → HCID 178441993, compound

HRID 2351874Notes

Reaction equation

HRID 2351874 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:15]=[CH:16][CH:17]=1)[O:5][CH:6]([CH3:14])[CH2:7][CH2:8][C:9]1[NH:13][N:12]=[N:11][N:10]=1.Cl.Cl[CH2:20][C:21]1[CH:30]=[CH:29][C:28]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[N:22]=1.[OH-].[Na+].C1COCC1>CN(C=O)C.O>[N:22]1[C:23]2[C:28](=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH:29]=[CH:30][C:21]=1[CH2:20][O:1][C:2]1[CH:3]=[C:4]([CH:15]=[CH:16][CH:17]=1)[O:5][CH:6]([CH3:14])[CH2:7][CH2:8][C:9]1[NH:13][N:12]=[N:11][N:10]=1

Participants

7

Reactant 4

HCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 30838232-(Chloromethyl)quinoline hydrochlorideHCID 178441992HCID 178441992, compound

Product 1

HCID 178441993HCID 178441993, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of 2.34 g (0.01 mol) 5-[3-(3-hydroxyphenoxy)butyl]tetrazole, 2.13 g (0.01 mol) 2-chloromethylquinoline hydrochloride and 12 ml (2N, NaOH) in 20 ml DMF and 20 ml THF is heated over a steam bath for a period of 24 hours. The reaction mixture is poured into water and extracted with ether. The ether extract is washed with water, dried over MgSO4 and concentrated to dryness under reduced pressure. The residue is passed through a silica gel column using hexane/ethyl acetate (3:1) as eluent. Evaporation of eluent gives 5-[3-(3-(2-quinolylmethyloxy)phenoxy)butyl]tetrazole. (M.P. 147°-149° C.).

Workup

  1. extractionextracted with ether
  2. extractionThe ether extract
  3. washis washed with water
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated to dryness under reduced pressure
  6. customEvaporation of eluent

Sources & evidence

ORD record
ord-9a593d8cafad45a8b17003ef82b9edce
Source dataset
uspto-grants-1989_10
Patent number
US04874769

Reaction notes

Loading…