2-chloro-3,5-bis(trifluoromethyl)aniline → HCID 86720676, compound

HRID 1749132Notes

Reaction equation

HRID 1749132 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].[Cl:17][C:18]1[C:24]([C:25]([F:28])([F:27])[F:26])=[CH:23][C:22]([C:29]([F:32])([F:31])[F:30])=[CH:21][C:19]=1[NH2:20]>N1C=CC=CC=1>[C:1]([C:5]1[CH:10]=[C:9]([CH3:11])[C:8]([S:12]([NH:20][C:19]2[CH:21]=[C:22]([C:29]([F:30])([F:31])[F:32])[CH:23]=[C:24]([C:25]([F:26])([F:27])[F:28])[C:18]=2[Cl:17])(=[O:14])=[O:13])=[C:7]([CH3:16])[CH:6]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 27574292-chloro-3,5-bis(trifluoromethyl)anilineHCID 38685064-tert-butyl-2,6-dimethylbenzenesulfonyl chloride

Product 1

HCID 86720676HCID 86720676, compoundYield 14.4%

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 2-chloro-3,5-bis(trifluoromethyl)aniline (0.101 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 (0.027 g, 14% yield). LCMS (M+Na) 510.

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-ecce0bbe2d5f4e0589f392c4f0a33a09
Source dataset
uspto-grants-2015_10
Patent number
US09156781B2

Reaction notes

Loading…