Dimethyl Sulfoxide → 2-Chloro-4-pyridinecarboxaldehyde

HRID 324043

反応式

HRID 324043 の反応式
C(Cl)(=O)C(Cl)=O.CS(C)=O.[Cl:11][C:12]1[CH:17]=[C:16]([CH2:18][OH:19])[CH:15]=[CH:14][N:13]=1.C(N(CC)CC)C>C(Cl)Cl.O>[Cl:11][C:12]1[CH:17]=[C:16]([CH:18]=[O:19])[CH:15]=[CH:14][N:13]=1

参加物

7

反応物 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 7062237(2-Chloropyridin-4-yl)methanol

生成物 1

HCID 27629942-Chloro-4-pyridinecarboxaldehyde

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6344Dichloromethane溶媒3 回

実験手順

To a solution of oxalyl chloride (42.2 ml) in methylene chloride (1100 ml) is added dropwise a solution of dimethyl sulfoxide (68.7 ml) in methylene chloride (220 ml) at −60° C. to −50° C., and thereto is further added dropwise a solution of 2-chloro-4-hydroxymethylpyridine (63.2 g) in methylene chloride (440 ml) at the same temperature. The mixture is stirred for 15 minutes, and thereto is added dropwise triethylamine (306.6 ml) at the same temperature. The mixture is stirred for five minutes, and warmed to room temperature. After the reaction is complete, to the reaction mixture is added water (2.2 liters). The methylene chloride layer is separated, and the aqueous layer is extracted again with methylene chloride (2.2 liters). The methylene chloride layers are combined, and washed with a saturated aqueous sodium hydrogen carbonate solution, dried, and concentrated under reduced pressure to remove the solvent to give 2-chloropyridine-4-carbaldehyde.

後処理

  1. stirringThe mixture is stirred for five minutes
  2. customThe methylene chloride layer is separated
  3. extractionthe aqueous layer is extracted again with methylene chloride (2.2 liters)
  4. washwashed with a saturated aqueous sodium hydrogen carbonate solution
  5. customdried
  6. concentrationconcentrated under reduced pressure
  7. customto remove the solvent

出典と根拠

ORDレコード
ord-c17bac9bc2394de596d47eb8aefdcd61
出典データセット
uspto-grants-2001_04
特許番号
US06214996B1

関連ノート

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