4-(Difluoromethoxy)aniline → 2-Butyl-5-(3-chlorophenyl)-4-{[4-(difluoromethoxy)phenyl]amino}isothiazol-3(2H)-one 1,1-dioxide

HRID 729296

반응식

HRID 729296 반응식
[CH2:1]([N:5]1[C:9](=[O:10])[C:8](Cl)=[C:7]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([Cl:18])[CH:13]=2)[S:6]1(=[O:20])=[O:19])[CH2:2][CH2:3][CH3:4].[F:21][CH:22]([F:31])[O:23][C:24]1[CH:30]=[CH:29][C:27]([NH2:28])=[CH:26][CH:25]=1>CC#N>[CH2:1]([N:5]1[C:9](=[O:10])[C:8]([NH:28][C:27]2[CH:29]=[CH:30][C:24]([O:23][CH:22]([F:21])[F:31])=[CH:25][CH:26]=2)=[C:7]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([Cl:18])[CH:13]=2)[S:6]1(=[O:20])=[O:19])[CH2:2][CH2:3][CH3:4]

참가 물질

4

반응물 2

HCID 7373634-(Difluoromethoxy)anilineHCID 68661625HCID 68661625, 화합물

생성물 1

HCID 116554612-Butyl-5-(3-chlorophenyl)-4-{[4-(difluoromethoxy)phenyl]amino}isothiazol-3(2H)-one 1,1-dioxide수율 73%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

반응 조건

온도
160 °C

실험 절차

2-Butyl-4-chloro-5-(3-chlorophenyl)isothiazol-3(2H)-one 1,1-dioxide (0.250 g, 0.75 mmol) and 4-(difluoromethoxy)aniline (0.238 g, 1.50 mmol) were mixed in MeCN (2 mL) and heated in a microwave reactor at 160° C. for 60 mins. The reaction mixture was evaporated and the residue was purified on a Horizon TM flash system using Heptane and EetOAc as eluant giving the title compound (0.25 g, 72.9%). 1H-NMR (500 MHz, CDCl3): δ 7.25-7.1 (m, 4H), 7.0 (s, 1H), 6.9-6.7 (dd, 4H), 6.4 (t, 1H, J=Hz), 3.8 (t, 2H), 1.95-1.8 (m, 2H), 1.55-1.45 (m, 2H), 1.05 (t, 3H); 13C-NMR (125 MHz, CDCl3): δ179.6, 159.0, 134.4, 133.3, 132.0, 129.9, 129.6, 129.6, 127.3, 124.3, 120.4, 115.9, 40.6, 30.4, 23.6, 20.3, 13.7; Mass Spectrum: M−H+ 456.

후처리

  1. customThe reaction mixture was evaporated
  2. customthe residue was purified on a Horizon TM flash system

출처 및 근거

ORD 기록
ord-049b4f5c35354f6ba826ae9fcecb6c61
출처 데이터셋
uspto-grants-2009_09
특허 번호
US07582629B2

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