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

HRID 724833

반응식

HRID 724833 반응식
[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

참가 물질

6

반응물 4

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

생성물 1

HCID 420843N-Methyl-N-phenyl-glycine수율 73%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

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%).

후처리

  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)

출처 및 근거

ORD 기록
ord-bf036da53cfd4e94b30a013dbb28b1dd
출처 데이터셋
uspto-grants-1998_01
특허 번호
US05705504

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