Sodium Iodide → HCID 14763125, 화합물

HRID 275130노트

반응식

HRID 275130 반응식
[N+:1]([C:4]1[CH:5]=[CH:6][C:7]2[O:12][CH2:11][CH2:10][NH:9][C:8]=2[CH:13]=1)([O-:3])=[O:2].Br[CH2:15][C:16]1[CH:25]=[CH:24][C:19]([C:20]([O:22][CH3:23])=[O:21])=[CH:18][C:17]=1[O:26][CH3:27].C(=O)([O-])[O-].[K+].[K+].[I-].[Na+]>CC(C)=O>[CH3:27][O:26][C:17]1[CH:18]=[C:19]([CH:24]=[CH:25][C:16]=1[CH2:15][N:9]1[C:8]2[CH:13]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=[CH:6][C:7]=2[O:12][CH2:11][CH2:10]1)[C:20]([O:22][CH3:23])=[O:21]

참가 물질

6

반응물 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 2759828Methyl 4-(bromomethyl)-3-methoxybenzoateHCID 70622256-nitro-3,4-dihydro-2H-1,4-benzoxazine

생성물 1

HCID 14763125HCID 14763125, 화합물수율 84%

시약·촉매·용매 1

HCID 180Acetone용매

실험 절차

A mixture of 6-nitro-2,3-dihydrobenz-1,4-oxazine (0.45 g.), methyl 4-bromomethyl-3-methoxybenzoate (B) (0.65 g.), anhydrous potassium carbonate (0.35 g.), sodium iodide (0.38 g.) and acetone (25 ml.) was stirred and heated under reflux for 48 hours, under an atmosphere of nitrogen. The cooled reaction mixture was separated by filtration. The residue was washed with acetone, and the filtrate and washings were evaporated. The resulting solid was dissolved in dichloromethane and residual solid removed by filtration. The filtrate was evaporated. The product was purified by flash chromatography on silica gel (3 cm. diameter column), eluting with 1:10 v/v ethyl acetate: toluene, to give methyl 3-methoxy-4-(6-nitro-2,3-dihydrobenz-1,4-oxazin-4-ylmethyl)benzoate (G) (0.75 g., 84%), m.p. 130°-132° C.; NMR (80 MHz, CDCl3): 3.0(t,2H, OCH2.CH2N), 3.8(s,3H, OCH3), 3.95(s,3H, OCH3), 4.3(t, 2H, OCH2.CH2N), 4.5(s,2H, CH2.Ar), 6.8(d,1H), 7.5(m, 5H).

후처리

  1. temperatureheated
  2. temperatureunder reflux for 48 hours, under an atmosphere of nitrogen
  3. customThe cooled reaction mixture
  4. customwas separated by filtration
  5. washThe residue was washed with acetone
  6. customthe filtrate and washings were evaporated
  7. dissolutionThe resulting solid was dissolved in dichloromethane
  8. customresidual solid removed by filtration
  9. customThe filtrate was evaporated
  10. customThe product was purified by flash chromatography on silica gel (3 cm. diameter column)
  11. washeluting with 1:10 v/v ethyl acetate

출처 및 근거

ORD 기록
ord-62eea3f9fbb947429f40dbed005140ca
출처 데이터셋
uspto-grants-1995_02
특허 번호
US05391758

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