Sodium Hydroxide → HCID 497159, compound

HRID 1905650Notes

Reaction equation

HRID 1905650 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[NH:13][N:12]=[N:11][N:10]=2)=[CH:5][CH:4]=1.[OH-].[Na+].[N+](C1C=CC(S(O[CH:29]([I:32])[C:30]#[CH:31])(=O)=O)=CC=1)([O-])=O>CN(C)C=O>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[N:10]=[N:11][N:12]([CH2:31][C:30]#[C:29][I:32])[N:13]=2)=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 20215061HCID 20215061, compoundHCID 178489163HCID 178489163, compound

Product 1

HCID 497159HCID 497159, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In anhydrous dimethylformamide were stirred well 1.86 g (10 mmoles) of 5-(p-methoxyphenyl)tetrazole and 420 mg (10 mmoles) of sodium hydroxide to form a homogeneous solution. To this solution were added under ice-cooling 3.67 g (10 mmoles) of iodopropargyl p-nitrobenzenesulfonate and the reaction was continued for 4 hours. The reaction mixture was extracted with 200 ml of ethyl acetate and 100 ml of water, the ethyl acetate layer was washed with water, dried and concentrated under reduced pressure. The solid residue, thus obtained was recrystallized twice from methanol to give 2-(1'-iodopropyn-3'-yl)-5-(p-methoxyphenyl)tetrazole, Yield 2.06 g (60%), mp. 146.7°-149.8° C.

Workup

  1. customto form a homogeneous solution
  2. additionTo this solution were added under ice-
  3. extractionThe reaction mixture was extracted with 200 ml of ethyl acetate and 100 ml of water
  4. washthe ethyl acetate layer was washed with water
  5. customdried
  6. concentrationconcentrated under reduced pressure
  7. customThe solid residue, thus obtained
  8. customwas recrystallized twice from methanol

Sources & evidence

ORD record
ord-d4dce73cede64c678340c8e4b103065c
Source dataset
uspto-grants-1987_03
Patent number
US04647572

Reaction notes

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