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Benzylamine → N2,N4-Dibenzyl-3-nitro-6-trifluoromethyl-pyridine-2,4-diamine

HRID 639621
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인쇄 미리보기

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HRID 639621 반응식
[N+:1]([C:4]1[C:5](O)=[N:6][C:7]([C:11]([F:14])([F:13])[F:12])=[CH:8][C:9]=1O)([O-:3])=[O:2].CC[N:18]([CH2:21][CH3:22])CC.O(S(C(F)(F)F)(=O)=O)S(C(F)(F)F)(=O)=O.[CH2:38]([NH2:45])[C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1>C(Cl)Cl.CCOC(C)=O.CCCCC>[CH2:38]([NH:45][C:5]1[C:4]([N+:1]([O-:3])=[O:2])=[C:9]([NH:18][CH2:21][C:22]2[CH:4]=[CH:9][CH:8]=[CH:7][CH:11]=2)[CH:8]=[C:7]([C:11]([F:14])([F:13])[F:12])[N:6]=1)[C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

8

반응물 4

HCID 7504BenzylamineHCID 8471TriethylamineHCID 67749Trifluoromethanesulfonic anhydrideHCID 178526877HCID 178526877, 화합물

생성물 1

HCID 67453795N2,N4-Dibenzyl-3-nitro-6-trifluoromethyl-pyridine-2,4-diamine수율 160.3%

시약·촉매·용매 3

HCID 6344
Dichloromethane
용매
HCID 8003Pentane용매
HCID 8857Ethyl Acetate용매

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온도
0 °C

실험 절차

A second batch of 3-Nitro-6-trifluoromethyl-pyridine-2,4-diol (11.06 g, 49.4 mmol) was dissolved in DCM (100 mL) and Et3N (13.8 ml, 98.7 mmol) was added. The mixture was cooled to 0° C. and Tf2O (16.2 ml, 98.7 mmol) was added dropwise. The mixture was allowed to warm to room temperature and stirred for 1 hour. The reaction mixture was concentrated in vacuo and the residue was dissolved in THF (100 ml). BnNH2 (16.2 ml, 148 mmol) was added and the mixture was stirred at 50° C. for 24 h. The reaction mixture was cooled to room temperature and concentrated in vacuo. The residue was treated with water (100 ml) and extracted with EtOAc (200 ml). The extract was washed with brine (50 ml), dried over MgSO4 and concentrated in vacuo to give the crude (53 g). The two crudes were combined. Column chromatography through silica eluting with 95:5→90:10 Pentane:EtOAc gave the title compound (15.93 g) as a yellow solid.

후처리

  1. temperatureto warm to room temperature
  2. concentrationThe reaction mixture was concentrated in vacuo
  3. dissolutionthe residue was dissolved in THF (100 ml)
  4. stirringthe mixture was stirred at 50° C. for 24 h
  5. temperatureThe reaction mixture was cooled to room temperature
  6. concentrationconcentrated in vacuo
  7. additionThe residue was treated with water (100 ml)
  8. extractionextracted with EtOAc (200 ml)
  9. washThe extract was washed with brine (50 ml)
  10. dry with materialdried over MgSO4
  11. concentrationconcentrated in vacuo
  12. customto give the crude (53 g)

출처 및 근거

ORD 기록
ord-06b5712b7ffb473798c71c0e109f6be1
출처 데이터셋
uspto-grants-2010_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07691877B2

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