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

HRID 747370

反応式

HRID 747370 の反応式
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

参加物

6

反応物 4

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

生成物 1

HCID 220187754-(Pyridin-2-ylaminomethyl)-benzaldehyde収率 31%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒3 回

反応条件

温度
-78 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-23175e30e4ea4a7fbbd03d2edd9c2ef3
出典データセット
uspto-grants-2008_07
特許番号
US07396840B2

関連ノート

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