2-methyl-3,5-bis(trifluoromethyl)aniline → HCID 75203091, compound

HRID 1749129Notes

Reaction equation

HRID 1749129 reaction equation
[CH2:1]([C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([CH2:9][CH3:10])[C:4]=1[S:11](Cl)(=[O:13])=[O:12])[CH3:2].[CH3:15][C:16]1[C:22]([C:23]([F:26])([F:25])[F:24])=[CH:21][C:20]([C:27]([F:30])([F:29])[F:28])=[CH:19][C:17]=1[NH2:18]>N1C=CC=CC=1>[CH2:1]([C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([CH2:9][CH3:10])[C:4]=1[S:11]([NH:18][C:17]1[CH:19]=[C:20]([C:27]([F:28])([F:29])[F:30])[CH:21]=[C:22]([C:23]([F:24])([F:25])[F:26])[C:16]=1[CH3:15])(=[O:13])=[O:12])[CH3:2]

Participants

4

Reactant 2

HCID 27361592-methyl-3,5-bis(trifluoromethyl)anilineHCID 1679112391920-30-8

Product 1

HCID 75203091HCID 75203091, compoundYield 42.3%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

2,6-Diethylbenzenesulfonyl chloride (0.100 g, 0.430 mmol) was added to a solution of 2-methyl-3,5-bis(trifluoromethyl)aniline (0.106 g, 0.434 mmol) in dry pyridine (1 mL). The reaction was capped and stirred at room temperature for 1 day then stirred at 30° C. for 1 day. The reaction was then concentrated under vacuum. To this was added diethyl ether (60 mL) and the mixture was washed with 0.1 N HCl (3×20 mL) followed by 0.1 N NaOH (2×20 mL) then saturated NaCl (2×20 mL). After drying the organic layer over MgSO4, the solution was filtered and concentrated under vacuum. The crude compound was purified by silica gel chromatography using hexanes/ethyl acetate (4:1) to afford the title compound (0.080 g, 42% yield). LCMS (M+Na) 461.

Workup

  1. customThe reaction was capped
  2. stirringthen stirred at 30° C. for 1 day
  3. concentrationThe reaction was then concentrated under vacuum
  4. additionTo this was added diethyl ether (60 mL)
  5. washthe mixture was washed with 0.1 N HCl (3×20 mL)
  6. dry with materialAfter drying the organic layer over MgSO4
  7. filtrationthe solution was filtered
  8. concentrationconcentrated under vacuum
  9. customThe crude compound was purified by silica gel chromatography

Sources & evidence

ORD record
ord-cd06f6a397aa4839b4a4a26bb2249bc4
Source dataset
uspto-grants-2015_10
Patent number
US09156781B2

Reaction notes

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