Water → 4-bromo-1-(3-chloro-2-methylbenzyl)-6-nitro-1H-benzo[d]imidazole

HRID 1622463ノート

反応式

HRID 1622463 の反応式
[Br:1][C:2]1[C:10]2[N:9]=[CH:8][NH:7][C:6]=2[CH:5]=[C:4]([N+:11]([O-:13])=[O:12])[CH:3]=1.Br[CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[C:18]([Cl:22])[C:17]=1[CH3:23].C(=O)([O-])[O-].[K+].[K+].O>CN(C)C=O>[Br:1][C:2]1[C:10]2[N:9]=[CH:8][N:7]([CH2:15][C:16]3[CH:21]=[CH:20][CH:19]=[C:18]([Cl:22])[C:17]=3[CH3:23])[C:6]=2[CH:5]=[C:4]([N+:11]([O-:13])=[O:12])[CH:3]=1

参加物

6

反応物 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 105130911-(Bromomethyl)-3-chloro-2-methylbenzeneHCID 532566897-Bromo-5-nitro-1H-benzimidazole

生成物 1

HCID 866878264-bromo-1-(3-chloro-2-methylbenzyl)-6-nitro-1H-benzo[d]imidazole収率 38.8%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
60 °C

実験手順

Into a 250 mL round bottomed flask charged with 4-bromo-6-nitro-1H-benzo[d]imidazole (5 g, 20.66 mmol) in N,N-Dimethylformamide (DMF) (100 mL) was added 1-(bromomethyl)-3-chloro-2-methylbenzene (6.80 g, 31.0 mmol) and potassium carbonate (8.57 g, 62.0 mmol The resulting reaction mixture was stirred 1 h at 60° C., cooled to room temperature and poured into water, extracted with ethyl acetate, washed with water, brine, dried (MgSO4) and evaporated. The residue was purified on a silica gel cartridge and eluted with a gradient of 0% ethyl acetate/hexanes to 80% over 10 column volumes. The expected compound was collected and evaporated to yield 4-bromo-1-(3-chloro-2-methylbenzyl)-6-nitro-1H-benzo[d]imidazole (3.05 g, 8.01 mmol, 38.8% yield) as a tan solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 2.40 (s, 3H) 5.79 (s, 2H) 6.61 (d, J=7.58 Hz, 1H) 7.16 (t, J=7.83 Hz, 1H) 7.42 (d, J=7.58 Hz, 1H) 8.34 (d, J=2.02 Hz, 1H) 8.65 (d, J=2.02 Hz, 1H) 8.73 (s, 1H); LC/MS: MS (ES+) m/e 381 [M+H]+.

後処理

  1. customThe resulting reaction mixture
  2. temperaturecooled to room temperature
  3. extractionextracted with ethyl acetate
  4. washwashed with water, brine
  5. dry with materialdried (MgSO4)
  6. customevaporated
  7. customThe residue was purified on a silica gel cartridge
  8. washeluted with a gradient of 0% ethyl acetate/hexanes to 80% over 10 column volumes
  9. customThe expected compound was collected
  10. customevaporated

出典と根拠

ORDレコード
ord-c3ea7c5b01724181843f6bff3c894fe7
出典データセット
uspto-grants-2014_07
特許番号
US08778937B2

反応ノート

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