Sulfuric Acid → HCID 86738807, compound

HRID 354543Notes

Reaction equation

HRID 354543 reaction equation
N([O-])=O.[Na+].[Cl:5][C:6]([C:26]([F:29])([F:28])[F:27])=[CH:7][C@@H:8]1[C@H:10]([C:11]([O:13][CH2:14][C:15]2[C:20]([CH3:21])=[CH:19][CH:18]=[C:17](N)[C:16]=2[CH3:23])=[O:12])[C:9]1([CH3:25])[CH3:24].S(=O)(=O)(O)O.[I-:35].[K+]>O.[Cu]>[Cl:5][C:6]([C:26]([F:29])([F:28])[F:27])=[CH:7][C@@H:8]1[C@H:10]([C:11]([O:13][CH2:14][C:15]2[C:20]([CH3:21])=[CH:19][CH:18]=[C:17]([I:35])[C:16]=2[CH3:23])=[O:12])[C:9]1([CH3:25])[CH3:24]

Participants

7

Reactant 4

HCID 1118Sulfuric Acid2×HCID 4875Potassium IodideHCID 23668193Sodium NitriteHCID 86738802HCID 86738802, compound

Product 1

HCID 86738807HCID 86738807, compoundYield 81.3%

Reagents, catalysts & solvents 2

HCID 23978CopperCatalystHCID 962WaterSolvent3×

Procedure

A solution of sodium nitrite (12.7 g) in water (15 ml) was added dropwise to a stirred mixture of (3-amino-2,6-dimethylphenyl)methyl cis-3-(2-chloro-3,3,3-trifluoropropenyl)-2,2-dimethylcyclopropanecarboxylate (9.5 g, 0.025 mole) and concentrated sulfuric acid (20.9 g) in water (120 ml), while maintaining the temperature at 0°. The mixture was stirred at 0° for an additional 0.5 hour, and concentrated sulfuric acid (5 ml) was added. A solution of potassium iodide (34.8 g) in water (25 ml) was added dropwise, followed by copper powder (0.2 g). The reaction mixture was slowly heated to 70°. After heating at 70° for one hour the reaction mixture was allowed to cool and was stirred for 16 hours. The reaction mixture was then extracted with three 300 ml portions of methylene chloride. The combined extracts were washed twice with 500 ml of saturated aqueous sodium bisulfite solution and once with 500 ml of saturated aqueous sodium chloride solution, dried over magnesium sulfate, filtered, and the solvent evaporated to give (3-iodo-2,6-dimethylphenyl)methyl cis-3-(2-chloro-3,3,3-trifluoropropenyl)-2,2-dimethylcyclopropanecarboxylate (9.89 g).

Workup

  1. temperaturewhile maintaining the temperature at 0°
  2. temperatureThe reaction mixture was slowly heated to 70°
  3. temperatureAfter heating at 70° for one hour the reaction mixture
  4. temperatureto cool
  5. stirringwas stirred for 16 hours
  6. extractionThe reaction mixture was then extracted with three 300 ml portions of methylene chloride
  7. washThe combined extracts were washed twice with 500 ml of saturated aqueous sodium bisulfite solution and once with 500 ml of saturated aqueous sodium chloride solution
  8. dry with materialdried over magnesium sulfate
  9. filtrationfiltered
  10. customthe solvent evaporated

Sources & evidence

ORD record
ord-e06db08bd62b4824bca3292a118e3ef4
Source dataset
uspto-grants-1983_03
Patent number
US04375476

Reaction notes

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