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

HRID 62699ノート

反応式

HRID 62699 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-bc741af4a26c43ffb06e37aa6e257499
出典データセット
uspto-grants-2016_09
特許番号
US09447030B2

反応ノート

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