Sodium hydride → 4-Fluorobenzyl-6-methyl-1H-benzo[d][1,3]oxazine-2,4-dione

HRID 346585노트

반응식

HRID 346585 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+].[F:16][C:17]1[CH:24]=[CH:23][C:20]([CH2:21]Br)=[CH:19][CH:18]=1>CN(C=O)C>[F:16][C:17]1[CH:24]=[CH:23][C:20]([CH2:21][N:6]2[C:5]3[CH:12]=[CH:13][C:2]([CH3:1])=[CH:3][C:4]=3[C:9](=[O:10])[O:8][C:7]2=[O:11])=[CH:19][CH:18]=1

참가 물질

5

반응물 3

HCID 24758Sodium hydrideHCID 680214-Fluorobenzyl bromideHCID 2944785-Methylisatoic anhydride

생성물 1

HCID 865946424-Fluorobenzyl-6-methyl-1H-benzo[d][1,3]oxazine-2,4-dione수율 79%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매2회

실험 절차

A solution of Compound 11 (5 g, 28 mmol) in DMF was added slowly to a suspension of NaH (60% in mineral oil, 1.24 g, 31 mmol) in DMF and further stirred at room temperature for 1 h. Then, neat 4-fluorobenzyl bromide (3.81 mL, 31 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 solids were suspended in hexane, sonicated briefly, filtered, and washed by hexane to yield 6.3 g (79%) of white solids. M.P. 153° C. 1H NMR (DMSO-d6): δ 2.32 (s, 3H), 5.24 (s, 2H), 7.14–7.17 (m, 3H), 7.44 (m, 2H), 7.54 (dd, J=1.7, 8.2 Hz, 1H), 7.83 (d, J=1.2 Hz, 1H). Anal. (C16H12FNO3) 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-64048d0233c443eaa08149699e05cae3
출처 데이터셋
uspto-grants-2007_02
특허 번호
US07173036B2

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