Iodine → HCID 19882803, compound

HRID 846508Notes

Reaction equation

HRID 846508 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[C:5]([O:9][CH2:10][C:11]#[CH:12])=[CH:4][C:3]=1[N:13]1[C:17](=[O:18])[N:16]([CH2:19][CH2:20][CH3:21])[N:15]=[N:14]1.[OH-].[Na+].[I:24]I>CO>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[C:5]([O:9][CH2:10][C:11]#[C:12][I:24])=[CH:4][C:3]=1[N:13]1[C:17](=[O:18])[N:16]([CH2:19][CH2:20][CH3:21])[N:15]=[N:14]1

Participants

5

Reactant 3

HCID 807IodineHCID 14798Sodium HydroxideHCID 19882808HCID 19882808, compound

Product 1

HCID 19882803HCID 19882803, compoundYield 20.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent3×

Procedure

To a cold solution of 0.5 g (0.00153 mole) of 1-[2,4-dichloro-5-(2-propynyloxy)phenyl]-1,4-dihydro-4-propyl-5H-tetrazol-5-one in 20 mL of methanol was added 2 mL of a saturated aqueous solution of sodium hydroxide and an additional 10 mL of methanol. To this mixture was added a solution of 0.39 g (0.00153 mole) of iodine in 5 mL of methanol. After complete addition, the reaction mixture was allowed to warm to room temperature and was stirred for approximately 18 hours. The reaction mixture was filtered and a solid collected. The solid was purified by column chromatography to yield 0.14 g of 1-[2,4-dichloro-5-(3-iodo-2-propynyloxy)phenyl]-1,4-dihydro-4-propyl-5H-tetrazol-5-one as a solid, mp 134°-138° C.

Workup

  1. additionAfter complete addition
  2. filtrationThe reaction mixture was filtered
  3. customa solid collected
  4. customThe solid was purified by column chromatography

Sources & evidence

ORD record
ord-ce67a136468f4709890d58ad7641ba5e
Source dataset
uspto-grants-1992_08
Patent number
US05136868

Reaction notes

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