2,4-Dimethoxybenzylamine → 2-(2,4-dimethoxybenzylamino)carbonyl-3-(4-nitrophenyl)-1H-pyrrole

HRID 227682

반응식

HRID 227682 반응식
[CH3:1][O:2][C:3]1[CH:10]=[C:9]([O:11][CH3:12])[CH:8]=[CH:7][C:4]=1[CH2:5][NH2:6].C[Al](C)C.[N+:17]([C:20]1[CH:25]=[CH:24][C:23]([C:26]2[CH:30]=[CH:29][NH:28][C:27]=2[C:31](OC)=[O:32])=[CH:22][CH:21]=1)([O-:19])=[O:18]>C1(C)C=CC=CC=1.C(OCC)(=O)C.C(#N)C>[CH3:1][O:2][C:3]1[CH:10]=[C:9]([O:11][CH3:12])[CH:8]=[CH:7][C:4]=1[CH2:5][NH:6][C:31]([C:27]1[NH:28][CH:29]=[CH:30][C:26]=1[C:23]1[CH:22]=[CH:21][C:20]([N+:17]([O-:19])=[O:18])=[CH:25][CH:24]=1)=[O:32]

참가 물질

7

반응물 3

HCID 5972502,4-DimethoxybenzylamineHCID 16682925TrimethylaluminumHCID 18616331methyl 3-(4-nitrophenyl)-1H-pyrrole-2-carboxylate

생성물 1

HCID 577568782-(2,4-dimethoxybenzylamino)carbonyl-3-(4-nitrophenyl)-1H-pyrrole수율 64.9%

시약·촉매·용매 3

HCID 1140Toluene용매2회HCID 6342Acetonitrile용매HCID 8857Ethyl Acetate용매

반응 조건

온도
20 °C

실험 절차

To 2.435 cm3 (15.84 mmol) of 2,4-dimethoxybenzylamine dissolved in 65 cm3 of toluene are added, at a temperature in the region of 20° C. under an argon atmosphere, 10.3 cm3 (20.59 mmol) of a 2M solution of trimethylaluminium in toluene, followed by addition of 1.95 g (7.92 mmol) of methyl 3-(4-nitrophenyl)-1H-pyrrole-2-carboxylate. After stirring for 1 hour at a temperature in the region of 20° C. and then for 16 hours at a temperature in the region of 60° C., the reaction mixture is diluted with 170 cm3 of ethyl acetate. The resulting solution is washed successively with three times 70 cm3 of saturated aqueous ammonium chloride solution and twice 50 cm3 of water and then dried over anhydrous magnesium sulfate, filtered and concentrated to dryness under reduced pressure (2.7 kPa) to give a yellow solid, which is then stirred in 20 cm3 of acetonitrile at a temperature in the region of 5° C. for 30 minutes. After filtering through a No. 3 sinter funnel, the solid is washed with 10 cm3 of ice-cold acetonitrile and then dried under reduced pressure (2.7 kPa) at a temperature in the region of 35° C. for 3 hours to give 1.96 g of 2-(2,4-dimethoxybenzylamino)carbonyl-3-(4-nitrophenyl)-1H-pyrrole in the form of a yellow solid; ES+: m/z=382: [M+H]+; ES−: m/z=380: [M−H]−.

후처리

  1. additionare added, at a temperature in the region of 20° C. under an argon atmosphere
  2. waitfor 16 hours at a temperature in the region of 60° C.
  3. washThe resulting solution is washed successively with three times 70 cm3 of saturated aqueous ammonium chloride solution and twice 50 cm3 of water
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated to dryness under reduced pressure (2.7 kPa)
  7. customto give a yellow solid, which
  8. filtrationAfter filtering through a No
  9. wash3 sinter funnel, the solid is washed with 10 cm3 of ice-cold acetonitrile
  10. customdried under reduced pressure (2.7 kPa) at a temperature in the region of 35° C. for 3 hours

출처 및 근거

ORD 기록
ord-e99534bacea84e6baf689b8773f7cf87
출처 데이터셋
uspto-grants-2009_07
특허 번호
US07560571B2

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