Benzenamine, 3,5-bis(trifluoromethyl)- → HCID 75202965, compound

HRID 1749128Notes

Reaction equation

HRID 1749128 reaction equation
[C:1]([C:5]1[CH:10]=[C:9]([CH3:11])[C:8]([S:12](Cl)(=[O:14])=[O:13])=[C:7]([CH3:16])[CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[F:17][C:18]([F:31])([F:30])[C:19]1[CH:20]=[C:21]([CH:23]=[C:24]([C:26]([F:29])([F:28])[F:27])[CH:25]=1)[NH2:22]>N1C=CC=CC=1>[F:17][C:18]([F:30])([F:31])[C:19]1[CH:20]=[C:21]([NH:22][S:12]([C:8]2[C:9]([CH3:11])=[CH:10][C:5]([C:1]([CH3:4])([CH3:3])[CH3:2])=[CH:6][C:7]=2[CH3:16])(=[O:14])=[O:13])[CH:23]=[C:24]([C:26]([F:27])([F:29])[F:28])[CH:25]=1

Participants

4

Reactant 2

HCID 9480Benzenamine, 3,5-bis(trifluoromethyl)-HCID 38685064-tert-butyl-2,6-dimethylbenzenesulfonyl chloride

Product 1

HCID 75202965HCID 75202965, compoundYield 23%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

4-Tert-butyl-2,6-dimethyl-benzenesulfonyl chloride (0.100 g, 0.383 mmol) was added to a solution of 3,5-bis(trifluoromethyl)aniline (0.089 g, 0.387 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 (0.040 g, 23% yield). LCMS (M+Na) 476.

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-5d1214be971c41559278d12286f84a74
Source dataset
uspto-grants-2015_10
Patent number
US09156781B2

Reaction notes

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