Tetrahydrofuran → 4-bromo-N-[2,4-bis(methylthio)-6-methyl-3-pyridyl]butanamide

HRID 22884

반응식

HRID 22884 반응식
C(N(CC)CC)C.C1COCC1.[NH2:13][C:14]1[C:15]([S:23][CH3:24])=[N:16][C:17]([CH3:22])=[CH:18][C:19]=1[S:20][CH3:21].[Br:25][CH2:26][CH2:27][CH2:28][C:29](Cl)=[O:30]>O>[Br:25][CH2:26][CH2:27][CH2:28][C:29]([NH:13][C:14]1[C:15]([S:23][CH3:24])=[N:16][C:17]([CH3:22])=[CH:18][C:19]=1[S:20][CH3:21])=[O:30]

참가 물질

6

반응물 4

HCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 702254-Bromobutyryl chlorideHCID 99903926-Methyl-2,4-bis-methylsulfanylpyridin-3-ylamine

생성물 1

HCID 225921434-bromo-N-[2,4-bis(methylthio)-6-methyl-3-pyridyl]butanamide수율 66%

시약·촉매·용매 1

HCID 962Water용매

실험 절차

Triethylamine (206 mg, 2.04 mmol) was added to a THF (6 ml) solution of 3-amino-2,4-bis(methylthio)-6-methylpyridine (341 mg, 1.70 mmol), and 4-bromobutanoyl chloride (379 mg, 2.04 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 ethyl acetate. The organic layer was washed with water and then with a saturated aqueous solution of sodium chloride, and dried over sodium sulfate. Subsequently, the solvent was distilled off, and the resulting crude product was purified through silica gel chromatography (silica gel 75 g, eluent-hexane:acetone=5:1→3:1) to obtain 390 mg (yield 66%) of 4-bromo-N-[2,4-bis(methylthio)-6-methyl-3-pyridyl]butanamide as a colorless crystal (melting point: 139 to 140° C.).

후처리

  1. additionwas then slowly added
  2. temperaturedropwise while being cooled with ice
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with water
  5. dry with materialwith a saturated aqueous solution of sodium chloride, 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 75 g, eluent-hexane:acetone=5:1→3:1)

출처 및 근거

ORD 기록
ord-c12b1eb5f9fa48d18395bc047a0571bf
출처 데이터셋
uspto-grants-2005_02
특허 번호
US06849647B1

연결된 노트

불러오는 중…