2,4,6-Tris(1-methylethyl)benzenamine → HCID 86720675, compound

HRID 1749126Notes

Reaction equation

HRID 1749126 reaction equation
[F:1][C:2]([F:18])([F:17])[C:3]1[CH:4]=[C:5]([S:13](Cl)(=[O:15])=[O:14])[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1.[CH:19]([C:22]1[CH:28]=[C:27]([CH:29]([CH3:31])[CH3:30])[CH:26]=[C:25]([CH:32]([CH3:34])[CH3:33])[C:23]=1[NH2:24])([CH3:21])[CH3:20]>N1C=CC=CC=1>[F:1][C:2]([F:18])([F:17])[C:3]1[CH:4]=[C:5]([S:13]([NH:24][C:23]2[C:25]([CH:32]([CH3:33])[CH3:34])=[CH:26][C:27]([CH:29]([CH3:31])[CH3:30])=[CH:28][C:22]=2[CH:19]([CH3:21])[CH3:20])(=[O:15])=[O:14])[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1

Participants

4

Reactant 2

HCID 5198712,4,6-Tris(1-methylethyl)benzenamineHCID 5209453,5-Bis(trifluoromethyl)benzenesulphonyl chloride

Product 1

HCID 86720675HCID 86720675, compoundYield 73.4%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

3,5-Bis(trifluoromethyl)benzenesulfonyl chloride (0.037 g, 0.12 mmol) was added to a solution of 2,4,6-triisopropylaniline (0.025 g, 0.11 mmol) in dry pyridine (1 mL). After stirring at room temperature for 1 day, the reaction was concentrated under vacuum. To this was added ethyl acetate (30 mL), and the mixture was washed with 0.1 N HCl (2×20 mL) followed by saturated NaHCO3 (2×20 mL) then saturated NaCl (2×20 mL). After drying the organic layer over MgSO4, the mixture was concentrated under vacuum. The crude compound was purified by silica gel chromatography using hexanes/ethyl acetate (4:1) to afford the title compound (0.040 g. 71% yield). ES-MS negative Q1 (m/z) 494.6. 1H NMR (CDCl3) 8.14 (s, 2H), 8.05 (s, 1H), 6.96 (s, 2H), 6.05 (s, 1H), 2.97 (m, 2H), 2.88 (m, 1H), 1.23 (d, 6H), 0.98 (d, 12H).

Workup

  1. concentrationthe reaction was concentrated under vacuum
  2. additionTo this was added ethyl acetate (30 mL)
  3. washthe mixture was washed with 0.1 N HCl (2×20 mL)
  4. dry with materialAfter drying the organic layer over MgSO4
  5. concentrationthe mixture was concentrated under vacuum
  6. customThe crude compound was purified by silica gel chromatography

Sources & evidence

ORD record
ord-a5bc05359b7a4f3fab42ceeeeb3ea7e3
Source dataset
uspto-grants-2015_10
Patent number
US09156781B2

Reaction notes

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