1,1'-Carbonyldiimidazole → 7-bromo-4,4-dimethyl-1H-benzo[d][1,3]oxazin-2(4H)-one

HRID 2209289노트

반응식

HRID 2209289 반응식
[NH2:1][C:2]1[CH:7]=[C:6]([Br:8])[CH:5]=[CH:4][C:3]=1[C:9]([OH:12])([CH3:11])[CH3:10].C1N=CN([C:18](N2C=NC=C2)=[O:19])C=1>C1COCC1>[Br:8][C:6]1[CH:5]=[CH:4][C:3]2[C:9]([CH3:10])([CH3:11])[O:12][C:18](=[O:19])[NH:1][C:2]=2[CH:7]=1

참가 물질

4

반응물 2

HCID 682631,1'-CarbonyldiimidazoleHCID 571557062-(2-Amino-4-bromophenyl)propan-2-ol

생성물 1

HCID 468564867-bromo-4,4-dimethyl-1H-benzo[d][1,3]oxazin-2(4H)-one수율 89.8%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
60 °C

실험 절차

Into the solution of 2-(2-amino-4-bromophenyl)propan-2-ol (2.3 g) in THF (50 mL) was added CDI (1.95 g) at rt., then the mixture was warmed to 60° C. and stirred for overnight. After solvent removal, the residue was dissolved in ethyl acetate and washed with 1M of HCl(aq) and brine, and dried with dry agent. After removal of the solvent, the residue was crystallized from DCM and hexane to provide 2.3 g of 7-bromo-4,4-dimethyl-1H-benzo[d][1,3]oxazin-2(4H)-one 7.37 was synthesized. LCMS [M+H]+: 252.71. 1H NMR (400 MHz, Chloroform-d) δ 9.30 (s, 1H), 7.18 (d, d, J=8.2, 1.8 Hz, 1H), 7.06 (d, J=1.8 Hz, 1H), 6.99 (d, J=8.2 Hz, 1H), 1.71 (s, 6H).

후처리

  1. customAfter solvent removal
  2. dissolutionthe residue was dissolved in ethyl acetate
  3. washwashed with 1M of HCl(aq) and brine
  4. customdried
  5. customwith dry agent
  6. customAfter removal of the solvent
  7. customthe residue was crystallized from DCM and hexane

출처 및 근거

ORD 기록
ord-1b5f412ef6184224aafa7c9ad43213fe
출처 데이터셋
uspto-grants-2016_06
특허 번호
US09376441B2

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