Chloroform → 2-Bromo-N-(6-methyl-2,4-bis(methylthio)pyridin-3-yl)acetamide

HRID 22883ノート

反応式

HRID 22883 の反応式
C(N(CC)CC)C.C(Cl)(Cl)Cl.[NH2:12][C:13]1[C:14]([S:22][CH3:23])=[N:15][C:16]([CH3:21])=[CH:17][C:18]=1[S:19][CH3:20].[Br:24][CH2:25][C:26](Br)=[O:27]>O>[Br:24][CH2:25][C:26]([NH:12][C:13]1[C:14]([S:22][CH3:23])=[N:15][C:16]([CH3:21])=[CH:17][C:18]=1[S:19][CH3:20])=[O:27]

参加物

6

反応物 4

HCID 6212ChloroformHCID 8471TriethylamineHCID 61147Bromoacetyl bromideHCID 99903926-Methyl-2,4-bis-methylsulfanylpyridin-3-ylamine

生成物 1

HCID 222471492-Bromo-N-(6-methyl-2,4-bis(methylthio)pyridin-3-yl)acetamide収率 13%

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

Triethylamine (274 mg, 2.71 mmol) was added to a chloroform (10 ml) solution of 3-amino-2,4-bis(methylthio)-6-methylpyridine (492 mg, 2.46 mmol), and bromoacetyl bromide (521 mg, 2.58 mmol) was then slowly added thereto dropwise while being cooled with ice. The mixture was stirred at room temperature for 2 hours. The reaction mixture was diluted with water, and then extracted with methylene chloride. The organic layer was washed with 1N hydrochloric acid, water, an aqueous solution of sodium hydrogencarbonate, water and a saturated aqueous solution of sodium chloride in this order, and dried over sodium sulfate. Subsequently, the solvent was distilled off, and the resulting crude product was purified through silica gel chromatography (silica gel 25 g, eluent-hexane:acetone=7:1→5:1→3:1) to obtain 100 mg (yield 13%) of 2-bromo-N-[2,4-bis(methylthio)-6-methyl-3-pyridyl]acetamide as a colorless crystal (melting point: 171 to 172° C.).

後処理

  1. additionwas then slowly added
  2. temperaturedropwise while being cooled with ice
  3. extractionextracted with methylene chloride
  4. washThe organic layer was washed with 1N hydrochloric acid, water
  5. dry with materialan aqueous solution of sodium hydrogencarbonate, water and a saturated aqueous solution of sodium chloride in this order, and dried over sodium sulfate
  6. distillationSubsequently, the solvent was distilled off
  7. customthe resulting crude product was purified through silica gel chromatography (silica gel 25 g, eluent-hexane:acetone=7:1→5:1→3:1)

出典と根拠

ORDレコード
ord-b7a5ecabb1294d5d9b5fb1e1c452914c
出典データセット
uspto-grants-2005_02
特許番号
US06849647B1

反応ノート

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