Acetic Acid → 5-(Benzyloxy)-8-(2-chloroacetyl)-2H-benzo[b][1,4]oxazin-3(4H)-one

HRID 470986노트

반응식

HRID 470986 반응식
I(Cl)(=O)=O.I([Cl:8])(=O)=O.C([N+](C)(C)C)C1C=CC=CC=1.[C:20]([C:23]1[C:28]2[O:29][CH2:30][C:31](=[O:33])[NH:32][C:27]=2[C:26]([O:34][CH2:35][C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)=[CH:25][CH:24]=1)(=[O:22])[CH3:21].C(O)(=O)C.S(=O)(O)[O-].[Na+]>ClCCl.C(OCC)C.O>[CH2:35]([O:34][C:26]1[C:27]2[NH:32][C:31](=[O:33])[CH2:30][O:29][C:28]=2[C:23]([C:20](=[O:22])[CH2:21][Cl:8])=[CH:24][CH:25]=1)[C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1

참가 물질

8

반응물 4

HCID 176Acetic AcidHCID 23665763Sodium BisulfiteHCID 56924451Trimethylbenzylammonium DichloroiodateHCID 579889708-Acetyl-5-(benzyloxy)-2H-benzo[b][1,4]oxazin-3(4H)-one

생성물 1

HCID 579891615-(Benzyloxy)-8-(2-chloroacetyl)-2H-benzo[b][1,4]oxazin-3(4H)-one

시약·촉매·용매 3

HCID 962Water용매HCID 3283Diethyl Ether용매HCID 6344Dichloromethane용매

반응 조건

온도
65 °C

실험 절차

Benzyltrimethylammonium dichloroiodate (14.17 g) was added to a stirred solution of 8-acetyl-5-(benzyloxy)-2H-benzo[b][1,4]oxazin-3(4H)-one (example 11, step d) (5.5 g) in a mixture of dichloromethane (100 mL), acetic acid (33 mL) and water (5.5 mL) and the reaction mixture stirred at 65° C. for 20 h. The reaction was cooled to ambient temperature, treated with aqueous sodium bisulphite (5.78 g in 100 mL) and stirred for a further 30 min. The mixture was diluted with diethyl ether (200 mL) and the resulting solid collected by filtration, washed with water and diethyl ether, and dried under vacuum at 40° C. to afford the subtitled compound as a light brown solid. Yield 5.6 g.

후처리

  1. temperatureThe reaction was cooled to ambient temperature
  2. stirringstirred for a further 30 min
  3. filtrationthe resulting solid collected by filtration
  4. washwashed with water and diethyl ether
  5. customdried under vacuum at 40° C.

출처 및 근거

ORD 기록
ord-f2759356a33f4060a23f9a7c0eec75fd
출처 데이터셋
uspto-grants-2014_01
특허 번호
US08629271B2

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