Acetic Acid → N-Methyl-N-phenyl-glycine

HRID 724833

反応式

HRID 724833 の反応式
[C:1]1([NH:7][CH2:8][C:9]([OH:11])=[O:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C=O.[BH3-][C:15]#N.[Na+].CC(O)=O>C(#N)C>[CH3:15][N:7]([CH2:8][C:9]([OH:11])=[O:10])[C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

参加物

6

反応物 4

HCID 176Acetic AcidHCID 712FormaldehydeHCID 66025N-PhenylglycineHCID 5003444Sodium cyanoborohydride

生成物 1

HCID 420843N-Methyl-N-phenyl-glycine収率 73%

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

To a solution of N-phenylglycine (5 g, 33 mmol) and formaldehyde (37% aqueous solution, 20 mL) in acetonitrile (100 mL) was added NaBH3CN (6.8 g) and AcOH (2 mL) and the reaction mixture was stirred at room temperature overnight. Volatiles were removed in vacuo, the residue was acidified to pH=3-4 and extracted with CHCl3 several times. The combined organic extracts were dried and concentrated to afford a crude product (5.73 g), which was purified by chromatography on silica gel (EtOAc) to afford the title compound (3.96 g, 73%).

後処理

  1. customVolatiles were removed in vacuo
  2. extractionextracted with CHCl3 several times
  3. customThe combined organic extracts were dried
  4. concentrationconcentrated
  5. customto afford a crude product (5.73 g), which
  6. customwas purified by chromatography on silica gel (EtOAc)

出典と根拠

ORDレコード
ord-bf036da53cfd4e94b30a013dbb28b1dd
出典データセット
uspto-grants-1998_01
特許番号
US05705504

関連ノート

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