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

HRID 909868노트

반응식

HRID 909868 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)-one수율 91.2%

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 (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 filtered off, washed with water and further diethyl ether, and dried under vacuum at 40° C. to afford the subtitled compound as a light brown solid (5.6 g). 1H NMR (300 MHz, DMSO-d6) δ 10.41 (s, 1H), 7.55 (m, 2H), 7.44 (d, J=9.4 Hz, 1H), 7.39 (m, 2H), 7.32 (m, 1H), 6.95 (d, J=9.4 Hz, 1H), 5.30 (s, 2H), 4.96 (s, 2H), 4.69 (s, 2H).

후처리

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

출처 및 근거

ORD 기록
ord-9dace5de980e49439a7580e7761a01d4
출처 데이터셋
uspto-grants-2011_09
특허 번호
US08017602B2

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