Sodium Hydroxide → 2-Amino-6-(trifluoromethoxy)-5-benzothiazolol

HRID 482272노트

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HRID 482272 반응식
[NH2:1][C:2]1[S:3][C:4]2[CH:10]=[C:9]([O:11][C:12]([F:15])([F:14])[F:13])[C:8]([O:16]C)=[CH:7][C:5]=2[N:6]=1.[OH-].[Na+]>Br>[NH2:1][C:2]1[S:3][C:4]2[CH:10]=[C:9]([O:11][C:12]([F:15])([F:13])[F:14])[C:8]([OH:16])=[CH:7][C:5]=2[N:6]=1

참가 물질

4

반응물 2

HCID 14798Sodium HydroxideHCID 19063892HCID 19063892, 화합물

생성물 1

HCID 190638932-Amino-6-(trifluoromethoxy)-5-benzothiazolol수율 69.9%

시약·촉매·용매 1

HCID 260Hydrogen Bromide용매

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온도
20 °C

실험 절차

0.74 g of 2-amino-5-methoxy-6-(trifluoromethoxy)benzothiazole, in solution in 20 ml of 47% hydrobromic acid, are brought to reflux for 20 hours. After cooling to a temperature in the region of 20° C., the reaction mixture is poured in 20 ml of ice-cold water and the solution is basified using concentrated sodium hydroxide. The organic phase is then extracted with ethyl acetate, dried over magnesium sulphate, filtered and concentrated to dryness under reduced pressure (15 mm Hg, 2 kPa). The crude product thus obtained is purified by flash chromatography on a silica column, a dichloromethane/methanol (98/2 by volume) mixture being used as eluent. 0.49 g of 2-amino-5-hydroxy-6-(trifluoromethoxy)benzothiazole are thus isolated in the form of a white powder melting at 216° C. [(Analysis % calculated C: 38.40, H: 2.01, F: 22.78, N: 11.20, S: 12.82; % found C: 38.3, H: 1.9, F: 22.9, N: 11.2, S: 13.0); 1H N.M.R. spectrum (250 MHz, d6-(CD3)2SO, δ in ppm): 6.96 (broad s, 1H, aromatic H ortho to the OH), 7.54 (broad s, 2H, NH2), 7.61 (broad s, 1H, aromatic H meta to the OH), 9.95 (unresolved peak, 1H, OH)].

후처리

  1. temperatureto reflux for 20 hours
  2. extractionThe organic phase is then extracted with ethyl acetate
  3. dry with materialdried over magnesium sulphate
  4. filtrationfiltered
  5. concentrationconcentrated to dryness under reduced pressure (15 mm Hg, 2 kPa)
  6. customThe crude product thus obtained
  7. customis purified by flash chromatography on a silica column

출처 및 근거

ORD 기록
ord-5584a96ff730463d9505f0647d2e95ef
출처 데이터셋
uspto-grants-1998_08
특허 번호
US05795903

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