Dichloromethane → HCID 21329859, compound

HRID 614026Notes

Reaction equation

HRID 614026 reaction equation
[F:1][C:2]([F:16])([F:15])[C:3]1[CH:4]=[C:5]([CH:12]=[CH:13][CH:14]=1)[C:6]([N:9]=[C:10]=[O:11])([CH3:8])[CH3:7].[C:17]1([NH:23][OH:24])[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.Cl[CH2:26]Cl>>[F:1][C:2]([F:15])([F:16])[C:3]1[CH:4]=[C:5]([CH:12]=[CH:13][CH:14]=1)[C:6]([NH:9][C:10](=[O:11])[N:23]([O:24][CH3:26])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)([CH3:8])[CH3:7]

Participants

4

Reactant 3

HCID 6344Dichloromethane2×HCID 7518N-PhenylhydroxylamineHCID 21329853HCID 21329853, compound

Product 1

HCID 21329859HCID 21329859, compound

Procedure

A solution of 2.2 g of m-trifluoromethyl-α,α-dimethylbenzyl isocyanate in 10 ml of dichloromethane was added dropwise to a solution of 1.1 g of N-phenylhydroxylamine in 10 ml of dichloromethane over a period of 10 minutes. After completion of the addition, the mixture was stirred for 30 minutes and the solvent was removed by distillation. The resulting white crystals were dried well and dissolved in 10 ml of a methanolic solution of 600 mg of sodium methoxide. 2.0 g of methyl iodide was added to the solution and the mixture was heated under reflux for 2 hours. The reaction mixture was concentrated and extracted with water and benzene. The benzene layer was washed successively with 2N aqueous sodium hydroxide and water and dried over anhydrous sodium sulfate. The solvent was removed by distillation and the resulting crystals were then recrystallized from a mixture of benzene and hexane to obtain 2.4 g of the title compound.

Workup

  1. additionAfter completion of the addition
  2. customthe solvent was removed by distillation
  3. customThe resulting white crystals were dried well
  4. dissolutiondissolved in 10 ml of a methanolic solution of 600 mg of sodium methoxide
  5. addition2.0 g of methyl iodide was added to the solution
  6. temperaturethe mixture was heated
  7. temperatureunder reflux for 2 hours
  8. concentrationThe reaction mixture was concentrated
  9. extractionextracted with water and benzene
  10. washThe benzene layer was washed successively with 2N aqueous sodium hydroxide and water
  11. dry with materialdried over anhydrous sodium sulfate
  12. customThe solvent was removed by distillation
  13. customthe resulting crystals were then recrystallized from a mixture of benzene and hexane

Sources & evidence

ORD record
ord-df08abf2328a41e8b00490671a7da086
Source dataset
uspto-grants-1979_03
Patent number
US04143061

Reaction notes

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