2-Fluoro-5-methylphenyl isocyanate → 1-[4-(3-Chloro-4-cyanoisothiazol-5-yl)phenyl]-3-(2-fluoro-5-methylphenyl)urea

HRID 871003노트

반응식

HRID 871003 반응식
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[S:12][N:11]=[C:10]([Cl:13])[C:9]=2[C:14]#[N:15])=[CH:4][CH:3]=1.[F:16][C:17]1[CH:22]=[CH:21][C:20]([CH3:23])=[CH:19][C:18]=1[N:24]=[C:25]=[O:26]>C1COCC1>[Cl:13][C:10]1[C:9]([C:14]#[N:15])=[C:8]([C:5]2[CH:4]=[CH:3][C:2]([NH:1][C:25]([NH:24][C:18]3[CH:19]=[C:20]([CH3:23])[CH:21]=[CH:22][C:17]=3[F:16])=[O:26])=[CH:7][CH:6]=2)[S:12][N:11]=1

참가 물질

4

반응물 2

HCID 27333772-Fluoro-5-methylphenyl isocyanate2회HCID 866892235-(4-Aminophenyl)-3-chloroisothiazole-4-carbonitrile

생성물 1

HCID 866892241-[4-(3-Chloro-4-cyanoisothiazol-5-yl)phenyl]-3-(2-fluoro-5-methylphenyl)urea수율 90.3%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

A solution of 5-(4-Aminophenyl)-3-chloroisothiazole-4-carbonitrile (4.565 g, 19.4 mmol) and 2-fluoro-5-methylphenyl isocyanate (5.85 g, 38.7 mmol) in 100 mL of dry THF was heated to reflux overnight. TLC indicated presence of considerable amount of starting material. Additional 2 g of 2-fluoro-5-methylphenyl isocyanate was added and the reaction was continued for another 24 h. The reaction was cooled to RT. THF was removed in vacuo and the resulting solid was stirred in 200 mL of Et2O for 1 h. Product was collected by filtration and washed with Et2O/hexanes to afford a light yellow solid (6.78 g, 90%).

후처리

  1. temperatureto reflux overnight
  2. customTHF was removed in vacuo
  3. filtrationProduct was collected by filtration
  4. washwashed with Et2O/hexanes

출처 및 근거

ORD 기록
ord-2aaff343e1904d1aa8c5501c749b9629
출처 데이터셋
uspto-grants-2015_03
특허 번호
US08969583B2

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