Hydrochloric Acid → 2-(Hydroxyimino)-N-(2-iodophenyl)acetamide

HRID 2375514노트

반응식

HRID 2375514 반응식
[NH:1]1C2C(=CC=CC=2)[C:4](=[O:5])[C:2]1=O.Cl.NO.S([O-])([O-])(=O)=O.[Na+].[Na+].Cl.[I:23][C:24]1[CH:30]=[CH:29][CH:28]=[CH:27][C:25]=1[NH2:26].ClC(Cl)(Cl)C(O)[OH:34]>O>[OH:34][N:1]=[CH:2][C:4]([NH:26][C:25]1[CH:27]=[CH:28][CH:29]=[CH:30][C:24]=1[I:23])=[O:5]

참가 물질

8

반응물 6

HCID 313Hydrochloric AcidHCID 2707Chloral HydrateHCID 7054IsatinHCID 119952-IodoanilineHCID 24436Sodium SulfateHCID 443297Hydroxyamine hydrochloride

생성물 1

HCID 63998232-(Hydroxyimino)-N-(2-iodophenyl)acetamide

시약·촉매·용매 1

HCID 962Water용매

반응 조건

온도
55 °C

실험 절차

Intermediate 5 was prepared according to the method described by Yang et al. (J. Am. Chem. Soc., 1996, 118, 9557), and the cyclization to the isatin was carried out as described by Marvel and Hiers (Org. Synth. Coll. Vol. I, 327). Hydroxylamine hydrochloride (11.4 g, 0.165 mol) and sodium sulfate (52 g, 0.366 mol) were placed in a 1 L round-bottomed flask, and 310 mL water, 16 mL 2 M aqueous hydrochloric acid and 2-iodoaniline (Aldrich, 10 g, 46 mmol) were added. Chloral hydrate (9.1 g, 55 mmol) was then added, and the mixture was heated at 55° C. overnight, with stirring. After cooling to room temperature, the slightly lumpy precipitate was collected by filtration, washing once with water, and dried under vacuum to yield isonitroso intermediate 5 as a beige solid (11.0 g, 83% yield): 1H NMR (400 MHz, DMSO-D6) δ ppm 6.99 (t, J=7.71 Hz, 1H) 7.41 (t, 1H) 7.63 (s, 1H) 7.76 (dd, J=8.08, 1.26 Hz, 1H) 7.90 (dd, J=7.83, 1.26 Hz, 1H) 9.38 (s, 1H) 12.42 (s, 1H).

후처리

  1. temperatureAfter cooling to room temperature
  2. filtrationthe slightly lumpy precipitate was collected by filtration
  3. washwashing once with water
  4. customdried under vacuum

출처 및 근거

ORD 기록
ord-9193b632ae6449f596c9c3de891c6b02
출처 데이터셋
uspto-grants-2008_12
특허 번호
US07465799B2

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