Pyrrolidine → N-(2-amino-5-bromophenyl)pyrrolidine-1-carboxamide

HRID 62699

반응식

HRID 62699 반응식
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([N+:9]([O-])=O)=[C:6]([CH:8]=1)[NH2:7].ClC(Cl)(O[C:16](=[O:22])OC(Cl)(Cl)Cl)Cl.[NH:24]1[CH2:28][CH2:27][CH2:26][CH2:25]1>ClCCl>[NH2:9][C:5]1[CH:4]=[CH:3][C:2]([Br:1])=[CH:8][C:6]=1[NH:7][C:16]([N:24]1[CH2:28][CH2:27][CH2:26][CH2:25]1)=[O:22]

참가 물질

5

반응물 3

HCID 31268PyrrolidineHCID 94429TriphosgeneHCID 53147665-Bromo-2-nitroaniline

생성물 1

HCID 86712537N-(2-amino-5-bromophenyl)pyrrolidine-1-carboxamide수율 34.4%

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

To a solution of 5-bromo-2-nitroaniline (1 g, 4.61 mmol) in dichloromethane (15 mL) were added TEA (8.35 mL, 59.9 mmol, 1.3 eq.) and triphosgene (1.37 g, 4.61 mmol, 1 equiv.) at 0° C. The mixture was stirred for three hours at room temperature and the pyrrolidine (0.39 g, 5.53 mmol, 1.2 equiv.) was added slowly. The reaction was stirred for an additional two hours. The reaction crude was diluted with dichloromethane and washed with water and brine. The organic layers were dried over MgSO4, filtered and evaporated. The residue was purified by column chromatography on eluting ethyl acetate and hexane to allow N-(2-amino-5-bromophenyl)pyrrolidine-1-carboxamide (0.45 g, 31% yield).

후처리

  1. stirringThe reaction was stirred for an additional two hours
  2. customThe reaction crude
  3. washwashed with water and brine
  4. dry with materialThe organic layers were dried over MgSO4
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue was purified by column chromatography
  8. washon eluting ethyl acetate and hexane

출처 및 근거

ORD 기록
ord-bc741af4a26c43ffb06e37aa6e257499
출처 데이터셋
uspto-grants-2016_09
특허 번호
US09447030B2

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