Triethylamine → Tert-butyl 4-(N-hydroxycarbamimidoyl)-phenylcarbamate

HRID 56624

반응식

HRID 56624 반응식
[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]

참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 21645Hydroxylamine HClHCID 10130644Tert-butyl 4-cyanophenylcarbamate

생성물 1

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

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

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)

후처리

  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

출처 및 근거

ORD 기록
ord-2f4bc81327554caa957bda3a2531d281
출처 데이터셋
uspto-grants-2016_09
특허 번호
US09434690B2

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