Water → 2-chloro-6H-benzo[e]benzo[4,5]imidazo[1,2-c][1,3]oxazine

HRID 1776877ノート

反応式

HRID 1776877 の反応式
[NH:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[C:10]1[CH:15]=[C:14]([Cl:16])[CH:13]=[CH:12][C:11]=1[OH:17].Br[CH2:19]Br.C([O-])([O-])=O.[K+].[K+].O>CN(C=O)C>[Cl:16][C:14]1[CH:13]=[CH:12][C:11]2[O:17][CH2:19][N:1]3[C:5]4[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=4[N:3]=[C:2]3[C:10]=2[CH:15]=1

参加物

6

反応物 4

HCID 962WaterHCID 3024DibromomethaneHCID 11430Potassium CarbonateHCID 35112112-(1H-benzo[d]imidazol-2-yl)-4-chlorophenol

生成物 1

HCID 712956192-chloro-6H-benzo[e]benzo[4,5]imidazo[1,2-c][1,3]oxazine収率 36%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
80 °C

実験手順

A mixture of 2-(1H-benzo[d]imidazol-2-yl)-4-chlorophenol (80 mg, 0.33 mmol), dibromo-methane (341 mg, 1.96 mmol), K2CO3 (137 mg, 0.99 mmol) in DMF (6 mL) was allowed to stir at 80° C. for 12 hours. Water (20 mL) was added and the mixture was extracted with ethyl acetate. The organic layer was washed with brine and dried over Na2SO4. After being concentrated in vacuo, the resulting resulting residue was purified using prep-HPLC to provide 2-chloro-6H-benzo[e]benzo[4,5]imidazo[1,2-c][1,3]oxazine (30 mg, yield: 36%). 1H-NMR (Methanol-d4, 400 MHz) δ 8.07 (d, J=2.1 Hz, 1H), 7.83˜7.81 (m, 1H), 7.78˜7.75 (m, 1H), 7.63 (dd, J=8.8, 2.2 Hz, 1H), 7.54˜7.52 (m, 2H), 7.30 (d, J=8.8 Hz, 1H), 6.33 (s, 2H). MS (M+H)+: 257.

後処理

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with brine
  3. dry with materialdried over Na2SO4
  4. concentrationAfter being concentrated in vacuo
  5. customthe resulting resulting residue
  6. customwas purified

出典と根拠

ORDレコード
ord-8ac901c9555347bba995d32c66a993b0
出典データセット
uspto-grants-2016_02
特許番号
US09265773B2

反応ノート

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