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

HRID 22883노트

반응식

HRID 22883 반응식
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]

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 962Water용매

실험 절차

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.).

후처리

  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)

출처 및 근거

ORD 기록
ord-b7a5ecabb1294d5d9b5fb1e1c452914c
출처 데이터셋
uspto-grants-2005_02
특허 번호
US06849647B1

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