Sodium Hydroxide → 3-[(4-iodophenyl)methyl]-2-(1-methylethyl)-3,5,6,7-tetrahydro-4H-benzimidazol-4-one

HRID 1946545ノート

反応式

HRID 1946545 の反応式
[CH3:1][CH:2]([C:4]1[NH:8][C:7]2[CH2:9][CH2:10][CH2:11][C:12](=[O:13])[C:6]=2[N:5]=1)[CH3:3].Br[CH2:15][C:16]1[CH:21]=[CH:20][C:19]([I:22])=[CH:18][CH:17]=1.[OH-].[Na+]>C1(C)C=CC=CC=1.[Br-].C([N+](CCCC)(CCCC)CCCC)CCC>[I:22][C:19]1[CH:20]=[CH:21][C:16]([CH2:15][N:5]2[C:6]3[C:12](=[O:13])[CH2:11][CH2:10][CH2:9][C:7]=3[N:8]=[C:4]2[CH:2]([CH3:1])[CH3:3])=[CH:17][CH:18]=1

参加物

6

反応物 3

HCID 14798Sodium HydroxideHCID 9542584-Iodobenzyl bromideHCID 584601782-Isopropyl-5,6-dihydro-1H-benzo[d]imidazol-7(4H)-one

生成物 1

HCID 584602073-[(4-iodophenyl)methyl]-2-(1-methylethyl)-3,5,6,7-tetrahydro-4H-benzimidazol-4-one収率 55.7%

試薬・触媒・溶媒 2

HCID 74236Tetrabutylammonium Bromide触媒HCID 1140Toluene溶媒

実験手順

To Intermediate 56 (2nd alternative preparation) (5.4 g) in Toluene (120 mL) was added 1-(bromomethyl)-4-iodobenzene (9.00 g) and tetrabutylammonium bromide (4.88 g) then sodium hydroxide, 5M aq (66.7 mL). The mixture was then stirred at room temperature, stirring vigorously to mix the phases for 1.5 h. The mixture was partitioned between ethyl acetate and water. The brown solid was filtered. The 2 phases were separated and the aqueous layer extracted well with ethyl acetate. The combined organics were dried (hydrophobic frit) and evaporated. The sample was loaded in dichloromethane and purified by column chromatography (silica) using 0-100% ethyl acetate-cyclohexane. The appropriate fractions were combined and evaporated in vacuo to give the required product 6.65 g as a brown oil. LC/MS MH+ 395, Rt 2.88 min (5 min run).

後処理

  1. stirringstirring vigorously
  2. additionto mix the phases for 1.5 h
  3. customThe mixture was partitioned between ethyl acetate and water
  4. filtrationThe brown solid was filtered
  5. customThe 2 phases were separated
  6. extractionthe aqueous layer extracted well with ethyl acetate
  7. customThe combined organics were dried (hydrophobic frit)
  8. customevaporated
  9. custompurified by column chromatography (silica)
  10. customevaporated in vacuo

出典と根拠

ORDレコード
ord-e7ebde722fe740b8bd6b03202d3349e9
出典データセット
uspto-grants-2013_03
特許番号
US08399444B2

反応ノート

読み込み中…