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

HRID 1939160

반응식

HRID 1939160 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-ba780a7fc7f14b40b789b172ead3450f
출처 데이터셋
uspto-grants-1997_12
특허 번호
US05696110

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