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

HRID 2209289ノート

反応式

HRID 2209289 の反応式
[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

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
60 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-1b5f412ef6184224aafa7c9ad43213fe
出典データセット
uspto-grants-2016_06
特許番号
US09376441B2

反応ノート

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