2-(difluoromethoxy)-5-methylaniline → HCID 86665721, compound

HRID 1619494Notes

Reaction equation

HRID 1619494 reaction equation
[F:1][CH:2]([F:12])[O:3][C:4]1[CH:10]=[CH:9][C:8]([CH3:11])=[CH:7][C:5]=1[NH2:6].[CH3:13][O:14][C:15]1[CH:20]=[CH:19][C:18]([S:21](Cl)(=[O:23])=[O:22])=[CH:17][C:16]=1[CH:25]1[CH2:29][CH2:28][N:27]([C:30](=[O:35])[C:31]([F:34])([F:33])[F:32])[CH2:26]1>N1C=CC=CC=1>[F:1][CH:2]([F:12])[O:3][C:4]1[CH:10]=[CH:9][C:8]([CH3:11])=[CH:7][C:5]=1[NH:6][S:21]([C:18]1[CH:19]=[CH:20][C:15]([O:14][CH3:13])=[C:16]([CH:25]2[CH2:29][CH2:28][N:27]([C:30](=[O:35])[C:31]([F:34])([F:32])[F:33])[CH2:26]2)[CH:17]=1)(=[O:23])=[O:22]

Participants

4

Reactant 2

HCID 70193422-(difluoromethoxy)-5-methylanilineHCID 86665720HCID 86665720, compound

Product 1

HCID 86665721HCID 86665721, compoundYield 35.1%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

0.093 g of 2-(difluoromethoxy)-5-methylaniline (0,538 mmol, purchased at Fluorochem) were dissolved in 10 mL of pyridin. 0.2 g of 4-methoxy-3-(1-(2,2,2-trifluoroacetyl)pyrrolidin-3-yl)benzene-1-sulfonyl chloride (0.538 mmol) were slowly added. The reaction mixture was stirred at room temperature for 18 h, and the solvent was evaporated and several times co-destilled with toluene. The oily brown residue was dissolved in dichloromethane and washed with a 5% aqueous ammonium chloride solution. After washing with saturated aqueous sodium chloride solution, the organic layer was dried over sodium sulphate, filtered, and the solvent evaporated. The crude product was purified via silica gel chromatography using a 40 g Redisep-column with dichloromethane/methanol 0-20% to yield 0.096 g of the title compound.

Workup

  1. customthe solvent was evaporated
  2. dissolutionThe oily brown residue was dissolved in dichloromethane
  3. washwashed with a 5% aqueous ammonium chloride solution
  4. washAfter washing with saturated aqueous sodium chloride solution
  5. dry with materialthe organic layer was dried over sodium sulphate
  6. filtrationfiltered
  7. customthe solvent evaporated
  8. customThe crude product was purified via silica gel chromatography

Sources & evidence

ORD record
ord-01b30b8bd9394b4d917fe3453e7bea45
Source dataset
uspto-grants-2014_07
Patent number
US08772313B2

Reaction notes

Loading…