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

HRID 1689217ノート

反応式

HRID 1689217 の反応式
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

参加物

8

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 3283Diethyl Ether溶媒HCID 6344Dichloromethane溶媒

反応条件

温度
65 °C

実験手順

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.

後処理

  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.

出典と根拠

ORDレコード
ord-10509b74fbbf47b79616bde84c018369
出典データセット
uspto-grants-2012_04
特許番号
US08148373B2

反応ノート

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