Dichloromethane → Benzyl hydroxycarbamate

HRID 879030

반응식

HRID 879030 반응식
Cl.[NH2:2][OH:3].[C:4](=[O:7])(O)[O-:5].[Na+].C(Cl)Cl.Cl[C:13]([O:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[O:14]>O>[OH:3][NH:2][C:13](=[O:14])[O:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.[CH2:16]([O:15][C:13]([O:3][NH:2][C:4](=[O:7])[O:5][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[O:14])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

참가 물질

7

반응물 4

HCID 6344Dichloromethane3회HCID 10387Benzyl chloroformateHCID 443297Hydroxyamine hydrochlorideHCID 516892Sodium Bicarbonate

생성물 2

HCID 18907Benzyl hydroxycarbamate수율 70%HCID 11822737N,O-bis(benzyloxycarbonyl)hydroxylamine수율 13%

시약·촉매·용매 1

HCID 962Water용매

반응 조건

온도
2 °C

실험 절차

Hydroxylamine hydrochloride (8.31 g, 120 mmol) is dissolved in water (200 mL) followed by the introduction of sodium bicarbonate (17.7 g, 211 mmol). Then CH2Cl2 (200 mL) is added to the solution and resulting the mixture is cooled in an ice bath to 0-4° C. Benzyl chloroformate (16.7 mL, 117 mmol) is added with vigorous stirring while maintaining the temperature below 4° C. After addition is complete the reaction mixture is left to stir for 2 h. The biphasic reaction mixture is transferred into a separating funnel and CH2Cl2 is added until the organic phase clarified. The aqueous phase is extracted with CH2Cl2 (3×100 mL) and then washed with brine, dried over MgSO4 and concentrated to give a colourless solid. Flash column chromatography (silica gel, CH2Cl2 then ethyl acetate/petroleum spirits 3:7 then 1:0) affords 13.7 g (70%) of 51 as a colourless solid along with 4.60 g (13%) of 52 as a colourless oil. Spectroscopic data are identical to those reported above.

후처리

  1. customresulting the mixture
  2. temperaturewhile maintaining the temperature below 4° C
  3. additionAfter addition
  4. waitis left
  5. stirringto stir for 2 h
  6. customThe biphasic reaction mixture
  7. customis transferred into a separating funnel
  8. extractionThe aqueous phase is extracted with CH2Cl2 (3×100 mL)
  9. washwashed with brine
  10. dry with materialdried over MgSO4
  11. concentrationconcentrated
  12. customto give a colourless solid

출처 및 근거

ORD 기록
ord-815dc066c4824d4dbf0f0e9c06d1b560
출처 데이터셋
uspto-grants-2015_03
특허 번호
US08987504B2

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