Benzyl Bromide → 1-Benzyl-6-methyl-1H-benzo[d][1,3]oxazine-2,4-dione

HRID 346584

반응식

HRID 346584 반응식
[CH3:1][C:2]1[CH:13]=[CH:12][C:5]2[NH:6][C:7](=[O:11])[O:8][C:9](=[O:10])[C:4]=2[CH:3]=1.[H-].[Na+].[CH2:16](Br)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>CN(C=O)C>[CH2:16]([N:6]1[C:5]2[CH:12]=[CH:13][C:2]([CH3:1])=[CH:3][C:4]=2[C:9](=[O:10])[O:8][C:7]1=[O:11])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

참가 물질

5

반응물 3

HCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 2944785-Methylisatoic anhydride

생성물 1

HCID 210819161-Benzyl-6-methyl-1H-benzo[d][1,3]oxazine-2,4-dione수율 97%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매2회

실험 절차

A solution of Compound 11 (25 g, 141 mmol) in DMF was added slowly to a suspension of NaH (60% in mineral oil, 6.21 g, 155 mmol) in DMF and further stirred at room temperature for 1 h. Then, neat benzyl bromide (19.53 mL, 155 mmol) was added and the solution further stirred at room temperature for 3 h. The solution was poured into ice water, and the solids formed were filtered, washed several times by water, and dried. The solid was suspended in hexane, sonicated briefly, filtered, and washed by hexane to yield 36.5 g (97%) of white solids. M.P. 150° C. 1H NMR (DMSO-d6): δ 2.32 (s, 3H), 5.27 (s, 2H), 7.15 (d, J=8.7 Hz, 1H), 7.26–7.39 (m, 5H), 7.54 (dd, J=1.5, 8.7 Hz, 1H), 7.83 (d, J=1.5 Hz, 1H). Anal. (C16H13NO3) C, H, N.

후처리

  1. stirringthe solution further stirred at room temperature for 3 h
  2. customthe solids formed
  3. filtrationwere filtered
  4. washwashed several times by water
  5. customdried
  6. customsonicated briefly
  7. filtrationfiltered
  8. washwashed by hexane

출처 및 근거

ORD 기록
ord-5ce467f7e5fb4262b869e83c7b4868b7
출처 데이터셋
uspto-grants-2007_02
특허 번호
US07173036B2

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