Sodium Hydroxide → HCID 178436222、化合物

HRID 991595ノート

反応式

HRID 991595 の反応式
[NH2:1][C:2]1[C:10]2[NH:9][C:8]([CH3:11])=[N:7][C:6]=2[CH:5]=[CH:4][CH:3]=1.[CH2:12]([C:14]1[CH:21]=[CH:20][CH:19]=[C:18]([CH2:22][CH3:23])[C:15]=1[CH:16]=O)[CH3:13].[BH3-]C#N.[Na+].[OH-].[Na+]>CO.[Cl-].[Cl-].[Zn+2]>[CH2:22]([C:18]1[CH:19]=[CH:20][CH:21]=[C:14]([CH2:12][CH3:13])[C:15]=1[CH2:16][NH:1][C:2]1[C:10]2[NH:9][C:8]([CH3:11])=[N:7][C:6]=2[CH:5]=[CH:4][CH:3]=1)[CH3:23]

参加物

7

反応物 4

HCID 14798Sodium HydroxideHCID 5003444Sodium cyanoborohydrideHCID 131847782,6-DiethylbenzaldehydeHCID 178432166HCID 178432166、化合物

生成物 1

HCID 178436222HCID 178436222、化合物収率 41%

試薬・触媒・溶媒 2

HCID 3007855Zincchloride触媒HCID 887Methanol溶媒

実験手順

4-Amino-2-methylbenzimidazole (0.79 g, 5.4 mmol) and 2,6-diethylbenzaldehyde (1.1 g, 6.6 mmol) were dissolved in methanol (30 ml). ZnCl2 (0.9 g, 6.6 mmol) and subsequently NaBH3CN (0.42 g, 6.6 mmol) in small portions were added and the mixture was refluxed under argon for 3 hours and was stirred at room temperature for 16 h. The mixture was poured over an aqueous 1M NaOH solution (50 ml). The resultant yellow suspension was extracted with DCM and the organic solution was washed with brine, dried over Na2SO4 and then evaporated under reduced pressure. The oily residue (1.8 g) was purified by crystallization from a mixture of ethyl acetate and acetonitrile to give 0.65 g (41%) of the title compound.

後処理

  1. temperaturethe mixture was refluxed under argon for 3 hours
  2. extractionThe resultant yellow suspension was extracted with DCM
  3. washthe organic solution was washed with brine
  4. dry with materialdried over Na2SO4
  5. customevaporated under reduced pressure
  6. customThe oily residue (1.8 g) was purified by crystallization from a mixture of ethyl acetate and acetonitrile

出典と根拠

ORDレコード
ord-4455fb3659784a0da15e42715ebbaf7f
出典データセット
uspto-grants-2002_10
特許番号
US06465505B1

反応ノート

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