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

HRID 909868ノート

反応式

HRID 909868 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収率 91.2%

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 (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).

後処理

  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.

出典と根拠

ORDレコード
ord-9dace5de980e49439a7580e7761a01d4
出典データセット
uspto-grants-2011_09
特許番号
US08017602B2

反応ノート

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