p-Cyanobenzyl alcohol → N-Hydroxy-4-(hydroxymethyl)benzimidamide

HRID 1941874ノート

反応式

HRID 1941874 の反応式
[OH:1][CH2:2][C:3]1[CH:10]=[CH:9][C:6]([C:7]#[N:8])=[CH:5][CH:4]=1.Cl.[NH2:12][OH:13].C([O-])(O)=O.[Na+]>CO>[OH:13][N:12]=[C:7]([NH2:8])[C:6]1[CH:9]=[CH:10][C:3]([CH2:2][OH:1])=[CH:4][CH:5]=1

参加物

5

反応物 3

HCID 160549p-Cyanobenzyl alcoholHCID 443297Hydroxyamine hydrochlorideHCID 516892Sodium Bicarbonate

生成物 1

HCID 53437716N-Hydroxy-4-(hydroxymethyl)benzimidamide収率 101.8%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒2 回

実験手順

A solution of 4-(hydroxymethyl)benzonitrile (22.43 g, 0.1685 g), hydroxylamine hydrochloride (18.67 g, 0.2689 mol) and NaHCO3 (45.22 g, 0.538 mol) in methanol (250 mL) was heated to reflux overnight. Upon cooling, the heterogeneous mixture was filtered and the solids were washed with additional methanol. The filtrate was evaporated to dryness to afford an off-white solid. The solids were suspended in ˜75 mL hot methanol, then cooled to room temperature and filtered. The filtrate was evaporated to afford N′-hydroxy-4-(hydroxymethyl)benzimidamide (28.5 g) as a white solid. The material was used without further purification. The compound had an HPLC retention time=0.232 min. −Column: CHROMOLITH® SpeedROD 4.6×50 mm (4 min.); Solvent A=10% MeOH, 90% H2O, 0.2% H3PO4; Solvent B=90% MeOH, 10% H2O, 0.2% H3PO4. LC/MS M+1=167.3

後処理

  1. temperatureto reflux overnight
  2. temperatureUpon cooling
  3. filtrationthe heterogeneous mixture was filtered
  4. washthe solids were washed with additional methanol
  5. customThe filtrate was evaporated to dryness
  6. customto afford an off-white solid
  7. filtrationfiltered
  8. customThe filtrate was evaporated

出典と根拠

ORDレコード
ord-a3bfb01f27d442ed8e07de3525291c7d
出典データセット
uspto-grants-2013_03
特許番号
US08389509B2

反応ノート

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