Chloroacetyl chloride → Methyl 8-iodo-3-oxo-3,4-dihydro-2H-1,4-benzoxazine-6-carboxylate

HRID 14185

反応式

HRID 14185 の反応式
[NH2:1][C:2]1[CH:3]=[C:4]([CH:9]=[C:10]([I:13])[C:11]=1[OH:12])[C:5]([O:7][CH3:8])=[O:6].C(=O)(O)[O-].[Na+].Cl[CH2:20][C:21](Cl)=[O:22]>CC(CC(C)C)=O.O>[I:13][C:10]1[C:11]2[O:12][CH2:20][C:21](=[O:22])[NH:1][C:2]=2[CH:3]=[C:4]([C:5]([O:7][CH3:8])=[O:6])[CH:9]=1

参加物

5

反応物 3

HCID 6577Chloroacetyl chlorideHCID 516892Sodium BicarbonateHCID 21086158Methyl 3-amino-4-hydroxy-5-iodobenzoate

生成物 1

HCID 21086219Methyl 8-iodo-3-oxo-3,4-dihydro-2H-1,4-benzoxazine-6-carboxylate収率 91.8%

試薬・触媒・溶媒 1

HCID 22737866Isobutyl methyl ketone water溶媒

実験手順

To an ice-cold, stirred solution of Methyl 3-amino-4-hydroxy-5-iodobenzoate (2.3 g) and sodium bicarbonate (1.5 g) in 1:1 isobutyl methyl ketone/water (80 mL) was added chloroacetyl chloride (1.1 g), and the reaction mixture was stirred for 1 h. The mixture was warmed to room temperature and heated at reflux for 18 h. After overnight, a beige solid formed. The mixture was filtered, and washed with water and hexanes to give 2.4 g of the title compound: 1H NMR (300 MHz, DMSO-d6) δ 10.98, 7.89, 7.47, 4.79, 3.82.

後処理

  1. temperatureheated
  2. temperatureat reflux for 18 h
  3. waitAfter overnight
  4. customa beige solid formed
  5. filtrationThe mixture was filtered
  6. washwashed with water and hexanes

出典と根拠

ORDレコード
ord-2515c445bb234b29b90cc014bc2bc950
出典データセット
uspto-grants-2010_06
特許番号
US07727997B2

関連ノート

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