O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate → N-(4-Chloro-3-nitrobenzyl)-1-(trifluoromethyl)cyclopropanecarboxamide

HRID 1410212노트

반응식

HRID 1410212 반응식
[F:1][C:2]([F:10])([F:9])[C:3]1([C:6](O)=[O:7])[CH2:5][CH2:4]1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.Cl.[Cl:34][C:35]1[CH:40]=[CH:39][C:38]([CH2:41][NH2:42])=[CH:37][C:36]=1[N+:43]([O-:45])=[O:44]>CN(C=O)C>[Cl:34][C:35]1[CH:40]=[CH:39][C:38]([CH2:41][NH:42][C:6]([C:3]2([C:2]([F:10])([F:9])[F:1])[CH2:5][CH2:4]2)=[O:7])=[CH:37][C:36]=1[N+:43]([O-:45])=[O:44]

참가 물질

5

반응물 3

HCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 27783061-(Trifluoromethyl)cyclopropane-1-carboxylic acidHCID 18796739(4-Chloro-3-nitrobenzyl)amine hydrochloride

생성물 1

HCID 59529820N-(4-Chloro-3-nitrobenzyl)-1-(trifluoromethyl)cyclopropanecarboxamide

시약·촉매·용매 1

HCID 6228Dimethylformamide용매2회

실험 절차

TEA (21.7 mL; 156 mmol) was added to a mixture of 1-(trifluoromethyl)-cyclopropanecarboxylic acid (8.00 g; 51.9 mmol) and TBTU (16.7 g; 52 mmol) in DMF (40 mL). After 1 h at rt, a solution of (4-chloro-3-nitrophenyl)methylamine hydrochloride (11.6 g; 52 mmol) in DMF (70 mL) was added dropwise over 30 min. After 17 h at rt, the mixture was concentrated and the residue partitioned between water and MTBE. The organic layer was washed with water, dried over Na2SO4 and concentrated. The residue was purified by column chromatography to give the sub-title compound. Yield: 13.191 g (78%).

후처리

  1. waitAfter 17 h at rt
  2. concentrationthe mixture was concentrated
  3. customthe residue partitioned between water and MTBE
  4. washThe organic layer was washed with water
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated
  7. customThe residue was purified by column chromatography

출처 및 근거

ORD 기록
ord-3606a1ef0a06425e92d71fdd30d73eb0
출처 데이터셋
uspto-grants-2014_12
특허 번호
US08921405B2

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