Iodine chloride → HCID 118113175, compound

HRID 1485079Notes

Reaction equation

HRID 1485079 reaction equation
[CH:1]1([C:5]2[CH:11]=[CH:10][C:8]([NH2:9])=[CH:7][C:6]=2[C:12]([F:15])([F:14])[F:13])[CH2:4][CH2:3][CH2:2]1.C(=O)([O-])O.[Na+].[I:21]Cl.S(S([O-])=O)([O-])(=O)=O.[Na+].[Na+]>C(Cl)(Cl)Cl.O.CO>[CH:1]1([C:5]2[C:6]([C:12]([F:13])([F:14])[F:15])=[CH:7][C:8]([NH2:9])=[C:10]([I:21])[CH:11]=2)[CH2:2][CH2:3][CH2:4]1

Participants

8

Reactant 4

HCID 24640Iodine chlorideHCID 516892Sodium BicarbonateHCID 656671Sodium PyrosulfiteHCID 118113301HCID 118113301, compound

Product 1

HCID 118113175HCID 118113175, compoundYield 97.9%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 6212ChloroformSolvent2×

Procedure

To a mixture of the compound (1.34 g) obtained in step (2) above, sodium hydrogencarbonate (628 mg), chloroform (32.0 mL) and methanol (8.00 mL), a solution of iodine monochloride (1.21 g) in chloroform (8.00 mL) was added dropwise at room temperature over a period of 30 minutes. The resulting mixture was stirred at room temperature for two hours. After adding a solution of 25% sodium metabisulfite in water (20.0 g) under cooling with ice, the mixture was stirred at room temperature for 30 minutes. The reaction mixture was extracted with chloroform and the combined organic layers were dried over anhydrous magnesium sulfate. After removing the desiccant by filtration, the filtrate was concentrated under reduced pressure to give 4-cyclobutyl-2-iodo-5-(trifluoromethyl)aniline as a brown oil (2.08 g).

Workup

  1. temperatureunder cooling with ice
  2. stirringthe mixture was stirred at room temperature for 30 minutes
  3. extractionThe reaction mixture was extracted with chloroform
  4. dry with materialthe combined organic layers were dried over anhydrous magnesium sulfate
  5. customAfter removing the
  6. filtrationdesiccant by filtration
  7. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-f76b3ef955fa4d2aa42d8a8304b9b25c
Source dataset
uspto-grants-2016_08
Patent number
US09422240B2

Reaction notes

Loading…