Resorcinol → HCID 178441992, compound

HRID 2351873Notes

Reaction equation

HRID 2351873 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([OH:8])[CH:3]=1.Cl[CH:10]([CH3:18])[CH2:11][CH2:12][C:13]1[NH:17][N:16]=[N:15][N:14]=1.[OH-].[Na+].C1COCC1>CN(C=O)C.O>[OH:1][C:2]1[CH:3]=[C:4]([CH:5]=[CH:6][CH:7]=1)[O:8][CH:10]([CH3:18])[CH2:11][CH2:12][C:13]1[NH:17][N:16]=[N:15][N:14]=1

Participants

7

Reactant 4

HCID 5054ResorcinolHCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 178456124HCID 178456124, compound

Product 1

HCID 178441992HCID 178441992, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of 1.43 g (0.013 mol) 1,3-dihyroxybenzene, 2.1 g (0.013 mol) 5-(3-chlorobutyl)tetrazole and 15 ml (2N, NaOH) in 15 ml DMF and 50 ml THF are stirred overnight at 60° C. bath temperature. The reaction mixture is poured into water and extracted with ether. The ether extract is washed with water, dried and concentrated to dryness under reduced pressure. The residue is passed through a silica gel column using hexane/ethylacetate (3:1) as eluent. Evaporation of eluent gives the tetrazole product which is used directly in the next step.

Workup

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

Sources & evidence

ORD record
ord-d5e41190e859474e9ca87a56f60cf4af
Source dataset
uspto-grants-1989_10
Patent number
US04874769

Reaction notes

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