Hydrochloric Acid → HCID 14404071, compound

HRID 465491Notes

Reaction equation

HRID 465491 reaction equation
[N+:1]([CH3:4])([O-:3])=[O:2].CC(C)([O-])C.[K+].[I:11][C:12]1[CH:17]=[CH:16][C:15]([S:18]([O-:20])=[O:19])=[CH:14][CH:13]=1.[Na+].II.S([O-])([O-])=O.[Na+].[Na+].Cl>CN(C=O)C.O>[I:11][C:12]1[CH:17]=[CH:16][C:15]([S:18]([CH2:4][N+:1]([O-:3])=[O:2])(=[O:20])=[O:19])=[CH:14][CH:13]=1

Participants

9

Reactant 6

HCID 313Hydrochloric AcidHCID 807IodineHCID 6375NitromethaneHCID 24437Sodium SulfiteHCID 23665647Potassium tert-butoxideHCID 23666130HCID 23666130, compound

Product 1

HCID 14404071HCID 14404071, compoundYield 2.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

Nitromethane (12.0 g, 100 mmol) was added dropwise to a stirred solution of potassium t-butoxide (20 g, 178 mmol) in dry DMF (200 ml), the temperature being controlled at 0°-5° C. by external cooling. After addition was complete the mixture was stirred for an additional 30 minutes at 0°-5° C. Sodium 4-iodobenzenesulphinate (29.0 g, 100 mmol) was then added, followed by iodine (22.8 g, 90 mmol). The mixture was stirred at ambient temperature for 2 hours and then poured into water (3 liters). A concentrated solution of aqueous sodium sulphite was added to partially decolourise the reaction mixture, which was then acidified with 2M hydrochloric acid. The precipitated solid was collected by filtration, washed with water and then recrystallised 4 times from ethanol to give (4-iodophenylsulphonyl)nitromethane as a crystalline solid (0.8 g), m.p. 177°-179° C., microanalysis, found C, 25.56; H, 1.83; N, 4.18% C 7 H6INO4S requires: C, 25.70; H, 1.85; N 4.30%.

Workup

  1. custombeing controlled at 0°-5° C. by external cooling
  2. additionAfter addition
  3. stirringThe mixture was stirred at ambient temperature for 2 hours
  4. filtrationThe precipitated solid was collected by filtration
  5. washwashed with water
  6. customrecrystallised 4 times from ethanol

Sources & evidence

ORD record
ord-2dd956b5447f4f1c9ba5a6537a10c4cd
Source dataset
uspto-grants-1992_10
Patent number
US05153227

Reaction notes

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