Potassium Iodide → HCID 86647002, compound

HRID 1947779Notes

Reaction equation

HRID 1947779 reaction equation
[CH3:1][O:2][C:3](=[O:16])[C:4]1[C:9]([CH:10]2[CH:14](N)[CH2:13][O:12][O:11]2)=[CH:8][CH:7]=[CH:6][CH:5]=1.N([O-])=O.[Na+].[I-:21].[K+]>OS(O)(=O)=O.O>[CH3:1][O:2][C:3](=[O:16])[C:4]1[C:9]([CH:10]2[CH:14]([I:21])[CH2:13][O:12][O:11]2)=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

6

Reactant 3

HCID 4875Potassium IodideHCID 23668193Sodium NitriteHCID 86647003HCID 86647003, compound

Product 1

HCID 86647002HCID 86647002, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 1118Sulfuric AcidSolvent

Procedure

A solution of 5-amino-2,3-dioxolanebenzoic acid methyl ester (0.5 g 2.5 mmol) (Chemische Berichte 1971, 104(8), 2347) in H2SO4 (0.5 ml in 9.5 ml) at 0° C. is treated with a solution of sodium nitrite (0.21 ml, 3.1 mmol) in water (1 ml), stirred for 1 hour, treated with a solution of potassium iodide (1.24 g, 7.5 mmol) in water (2 ml), and stirred at 80° C. for 10 min. The reaction mixture is quenched with water and extracted with dichloromethane (20 ml). Organic layer is separated and washed with water (25 ml), dried with sodium sulphate, and evaporated to give 5-iodo-2,3-dioxolanebenzoic acid methyl ester which is directly used in the next step.

Workup

  1. stirringstirred at 80° C. for 10 min
  2. customThe reaction mixture is quenched with water
  3. extractionextracted with dichloromethane (20 ml)
  4. customOrganic layer is separated
  5. washwashed with water (25 ml)
  6. dry with materialdried with sodium sulphate
  7. customevaporated

Sources & evidence

ORD record
ord-1c7fda1b29f84e3c9dd7236426e735d2
Source dataset
uspto-grants-2013_03
Patent number
US08399490B2

Reaction notes

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