4-(Difluoromethoxy)aniline → HCID 11661761, compound

HRID 729278Notes

Reaction equation

HRID 729278 reaction equation
[CH2:1]([N:5]1[C:9](=[O:10])[C:8](Cl)=[C:7]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[S:6]1(=[O:19])=[O:18])[CH2:2][CH2:3][CH3:4].[F:20][CH:21]([F:30])[O:22][C:23]1[CH:29]=[CH:28][C:26]([NH2:27])=[CH:25][CH:24]=1>CC#N>[CH2:1]([N:5]1[C:9](=[O:10])[C:8]([NH:27][C:26]2[CH:28]=[CH:29][C:23]([O:22][CH:21]([F:20])[F:30])=[CH:24][CH:25]=2)=[C:7]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[S:6]1(=[O:19])=[O:18])[CH2:2][CH2:3][CH3:4]

Participants

4

Reactant 2

HCID 7373634-(Difluoromethoxy)anilineHCID 672426232-Butyl-4-chloro-5-phenylisothiazol-3(2H)-one 1,1-dioxide

Product 1

HCID 11661761HCID 11661761, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

2-Butyl-4-chloro-5-phenylisothiazol-3(2H)-one 1,1-dioxide (0.63 g, 2.1 mmol) and 4-(difluoromethoxy)-aniline (0.67 g, 4.2 mmol) were mixed in MeCN (4 mL, dry). The mixture was put in the microwave reactor at 160° C. for 1 h, then additional 1 h and then 1 h more. It was evaporated to dryness. The residue was purified by column chromatography (ISOLUTE SI, 50 g/150 mL), eluting with DCM/heptane (50:50, then 75:25), to give the title compound (0.688 g, 78%) as a yellow solid; 1H-NMR (400 MHz; CDCl3): δ 0.99 (t, 3H), 1.42-1.52 (m, 2H), 1.82-1.90 (m, 2H), 3.77 (t, 2H), 6.34 (t, 1H), 6.67 (d, 2H), 6.76 (d, 2H), 7.11-7.17 (m, 4H), 7.22-7.26 (m, 1H); Mass Spectrum: M−H+ 421.

Workup

  1. customadditional 1 h
  2. custom1 h
  3. customIt was evaporated to dryness
  4. customThe residue was purified by column chromatography (ISOLUTE SI, 50 g/150 mL)
  5. washeluting with DCM/heptane (50:50

Sources & evidence

ORD record
ord-832834f57c2648dbb92d0ef8cd128e92
Source dataset
uspto-grants-2009_09
Patent number
US07582629B2

Reaction notes

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