Benzenamine, 3,5-bis(trifluoromethyl)- → HCID 75203090, compound

HRID 1749130Notes

Reaction equation

HRID 1749130 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].[F:15][C:16]([F:29])([F:28])[C:17]1[CH:18]=[C:19]([CH:21]=[C:22]([C:24]([F:27])([F:26])[F:25])[CH:23]=1)[NH2:20]>N1C=CC=CC=1>[F:15][C:16]([F:28])([F:29])[C:17]1[CH:18]=[C:19]([NH:20][S:11]([C:4]2[C:3]([CH2:1][CH3:2])=[CH:8][CH:7]=[CH:6][C:5]=2[CH2:9][CH3:10])(=[O:13])=[O:12])[CH:21]=[C:22]([C:24]([F:25])([F:27])[F:26])[CH:23]=1

Participants

4

Reactant 2

HCID 9480Benzenamine, 3,5-bis(trifluoromethyl)-HCID 1679112391920-30-8

Product 1

HCID 75203090HCID 75203090, compoundYield 20.2%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

2,6-Diethylbenzenesulfonyl chloride (0.100 g, 0.430 mmol) was added to a solution of 3,5-bis(trifluoromethyl)aniline (0.099 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 triturated with hexanes (2×10 mL) to afford the title compound (0.037 g, 20% yield). LCMS (M+Na) 447.

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 triturated with hexanes (2×10 mL)

Sources & evidence

ORD record
ord-e45b16bfea784475b5bd0ea1e09499d7
Source dataset
uspto-grants-2015_10
Patent number
US09156781B2

Reaction notes

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