Dimethyl Sulfoxide → 4-(Pyridin-2-ylaminomethyl)-benzaldehyde

HRID 7186

반응식

HRID 7186 반응식
C(Cl)(=O)C(Cl)=O.CS(C)=O.[N:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[NH:17][CH2:18][C:19]1[CH:24]=[CH:23][C:22]([CH2:25][OH:26])=[CH:21][CH:20]=1.CCN(CC)CC>C(Cl)Cl>[N:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[NH:17][CH2:18][C:19]1[CH:24]=[CH:23][C:22]([CH:25]=[O:26])=[CH:21][CH:20]=1

참가 물질

6

반응물 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 22018543(4-((Pyridin-2-ylamino)methyl)phenyl)methanol

생성물 1

HCID 220187754-(Pyridin-2-ylaminomethyl)-benzaldehyde수율 31%

시약·촉매·용매 1

HCID 6344Dichloromethane용매3회

반응 조건

온도
-78 °C

실험 절차

To a solution of oxalyl chloride (0.9 ml, 10.32 mmol) in CH2Cl2 (15 ml) at −78° C. was added a solution of DMSO (1.5 ml, 21.11 mmol) in CH2Cl2 (10 ml) and the mixture allowed to stir for 20 min. at −78° C., after which [4-(Pyridin-2-ylaminomethyl)-phenyl]-methanol (1.1 g, 5.13 mmol) in CH2Cl2 (10 ml) was added dropwise. Stirring was continued for 2 hours and then Et3N (2.9 ml, 21.30 mmol) was added dropwise. The cooling bath was removed, stirring was continued for 3 h, and the mixture was diluted with 300 mL ethyl acetate, washed with sat. NaHCO3, brine and dried over Na2SO4. Evaporation of the solvent and purification of the residue by flash chromatography on silica gel, using 30% ethyl acetate in CH2Cl2, gave the title compound (335 mg, 31%) as a pure white solid.

후처리

  1. stirringStirring
  2. waitwas continued for 2 hours
  3. customThe cooling bath was removed
  4. stirringstirring
  5. waitwas continued for 3 h
  6. additionthe mixture was diluted with 300 mL ethyl acetate
  7. washwashed with sat. NaHCO3, brine
  8. dry with materialdried over Na2SO4
  9. customEvaporation of the solvent and purification of the residue by flash chromatography on silica gel

출처 및 근거

ORD 기록
ord-f466dc70f6664a43a2e59685051e375f
출처 데이터셋
uspto-grants-2006_08
특허 번호
US07084155B2

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