三乙胺 → Tert-butyl 4-(N-hydroxycarbamimidoyl)-phenylcarbamate

HRID 56624

反应方程式

HRID 56624 反应方程式
[Cl-].[OH:2][NH3+:3].C(N(CC)CC)C.[C:11]([O:15][C:16](=[O:26])[NH:17][C:18]1[CH:23]=[CH:22][C:21]([C:24]#[N:25])=[CH:20][CH:19]=1)([CH3:14])([CH3:13])[CH3:12]>C(O)C>[OH:2][N:3]=[C:24]([C:21]1[CH:20]=[CH:19][C:18]([NH:17][C:16](=[O:26])[O:15][C:11]([CH3:13])([CH3:12])[CH3:14])=[CH:23][CH:22]=1)[NH2:25]

参与物

5

反应物 3

HCID 8471三乙胺HCID 21645盐酸羟胺HCID 10130644N-BOC-4-氨基苯腈

产物 1

HCID 53439229Tert-butyl 4-(N-hydroxycarbamimidoyl)-phenylcarbamate

试剂、催化剂与溶剂 1

HCID 702乙醇溶剂

实验过程

At RT, 1.40 g (20.16 mmol, 2.2 eq.) of hydroxylammonium chloride and 2.81 ml (20.16 mmol, 2.2 eq.) of triethylamine were added to a solution of 2.0 g (9.16 mmol) of tert-butyl-(4-cyanophenyl)carbamate in 45 ml of ethanol. The reaction mixture was heated under reflux for 4 h and concentrated under reduced pressure. The residue was stirred with 100 ml of water at RT for 1 h. The reaction mixture was filtered and the filter cake was washed with water. The residue was dissolved in ethyl acetate. The aqueous phase that remained was separated off and the organic phase was dried (sodium sulphate), filtered and concentrated under reduced pressure. The crude product was used for the next step without purification. Yield: 2.10 g (purity 95%, 87% of theory)

后处理

  1. temperatureThe reaction mixture was heated
  2. temperatureunder reflux for 4 h
  3. concentrationconcentrated under reduced pressure
  4. filtrationThe reaction mixture was filtered
  5. washthe filter cake was washed with water
  6. dissolutionThe residue was dissolved in ethyl acetate
  7. customThe aqueous phase that remained was separated off
  8. dry with materialthe organic phase was dried (sodium sulphate)
  9. filtrationfiltered
  10. concentrationconcentrated under reduced pressure
  11. customThe crude product was used for the next step without purification

来源与证据

ORD记录
ord-2f4bc81327554caa957bda3a2531d281
来源数据集
uspto-grants-2016_09
专利号
US09434690B2

关联笔记

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