Methyl N-methylanthranilate → Methyl 2-(N-bromoacetyl-N-methylamino)benzoate

HRID 1939160

反応式

HRID 1939160 の反応式
[OH-].[Na+].[Br:3][CH2:4][C:5](Br)=[O:6].[CH3:8][NH:9][C:10]1[C:11](=[CH:16][CH:17]=[CH:18][CH:19]=1)[C:12]([O:14][CH3:15])=[O:13]>ClCCl>[Br:3][CH2:4][C:5]([N:9]([C:10]1[CH:19]=[CH:18][CH:17]=[CH:16][C:11]=1[C:12]([O:14][CH3:15])=[O:13])[CH3:8])=[O:6]

参加物

5

反応物 3

HCID 6826Methyl N-methylanthranilateHCID 14798Sodium HydroxideHCID 61147Bromoacetyl bromide

生成物 1

HCID 10085361Methyl 2-(N-bromoacetyl-N-methylamino)benzoate収率 73.2%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

Sodium hydroxide solution (1.5M, 50 ml) was added dropwise to an ice cooled mixture of bromoacetyl bromide (11 g) and methyl N-methylanthranilate (8.2 g) in dichloromethane (250 ml). After the addition was complete (15 min) stirring was continued at room temperature for 20 min. The organic phase was then separated, washed with 1N HCl (50 ml), brine (50 ml), NaHCO3 solution (50 ml), dried (MgSO4) and evaporated to give a colourless oil which crystallised on standing. Trituration with pet-ether (bp 60°-80°) followed by filtration afforded 10.4 g of product as a colourless solid. 1H NMR (360 MHz, CDCl3) δ: 3.23 (3H, s), 3.54 and 3.60 (2H, ABq J=11 Hz), 3.90 (3H, s), 7.40 (1H, d, J=8 Hz), 7.51 (1H, t, J=8 Hz), 7.65 (1H, t, J=8 Hz), 8.04 (1H, d, J=8 Hz).

後処理

  1. temperaturecooled
  2. additionAfter the addition
  3. custom(15 min)
  4. customThe organic phase was then separated
  5. washwashed with 1N HCl (50 ml), brine (50 ml), NaHCO3 solution (50 ml)
  6. dry with materialdried (MgSO4)
  7. customevaporated
  8. customto give a colourless oil which
  9. customcrystallised
  10. filtrationTrituration with pet-ether (bp 60°-80°) followed by filtration

出典と根拠

ORDレコード
ord-ba780a7fc7f14b40b789b172ead3450f
出典データセット
uspto-grants-1997_12
特許番号
US05696110

関連ノート

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