Chloroacetyl chloride → 8-bromo-3,4-dihydro-2H-1,4-benzoxazin-3-one

HRID 2175217ノート

反応式

HRID 2175217 の反応式
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Br:8])[C:3]=1[OH:9].C(=O)(O)[O-].[Na+].Cl[CH2:16][C:17](Cl)=[O:18]>C(#N)C.O.CCOC(C)=O>[Br:8][C:4]1[C:3]2[O:9][CH2:16][C:17](=[O:18])[NH:1][C:2]=2[CH:7]=[CH:6][CH:5]=1

参加物

7

反応物 3

HCID 6577Chloroacetyl chlorideHCID 516892Sodium BicarbonateHCID 155315062-Amino-6-bromophenol

生成物 1

HCID 218735338-bromo-3,4-dihydro-2H-1,4-benzoxazin-3-one収率 94%

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 6342Acetonitrile溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
0 °C

実験手順

To a solution of 2-amino-6-bromophenol (1 g, 5.32 mmol) in acetonitrile (10 mL) and water (10 mL) was added sodium bicarbonate (1.028 g, 12.23 mmol). The mixture was cooled to 0° C. and chloroacetyl chloride (0.554 mL, 6.91 mmol) was added dropwise. The reaction was refluxed overnight. After cooling to room temperature, the mixture was diluted with EtOAc, washed with water, dried over anhydrous MgSO4, filtered, and concentrated to afford the title compound (1.14 g, 94% yield) as a dark brown solid. 1H NMR (400 MHz, CDCl3) δ 8.22 (br. s, 1H), 7.23 (dd, J=8.0, 1.4 Hz, 1H), 6.86 (t, J=8.0 Hz, 1H), 6.76 (dd, J=7.9, 1.3 Hz, 1H), 4.74 (s, 2H).

後処理

  1. temperatureThe reaction was refluxed overnight
  2. temperatureAfter cooling to room temperature
  3. washwashed with water
  4. dry with materialdried over anhydrous MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated

出典と根拠

ORDレコード
ord-b3380e3769174ad9b564c6279e138203
出典データセット
uspto-grants-2015_06
特許番号
US09062028B2

反応ノート

読み込み中…