Methyl iodide → 2-[methyl-N-(methoxycarbonyl)amino]-6-(phenylthio)imidazo[1,2-a]pyridine

HRID 839640ノート

反応式

HRID 839640 の反応式
[CH3:1][O:2][C:3]([NH:5][C:6]1[N:7]=[C:8]2[CH:13]=[CH:12][C:11]([S:14][C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)=[CH:10][N:9]2[CH:21]=1)=[O:4].O1CCC[CH2:23]1.C([Li])CCC.CI>CCCCCC>[CH3:23][N:5]([C:6]1[N:7]=[C:8]2[CH:13]=[CH:12][C:11]([S:14][C:15]3[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=3)=[CH:10][N:9]2[CH:21]=1)[C:3]([O:2][CH3:1])=[O:4]

参加物

6

反応物 4

HCID 6328Methyl iodideHCID 8028TetrahydrofuranHCID 12414300Methyl [6-(phenylsulfanyl)imidazo[1,2-a]pyridin-2-yl]carbamateHCID 178418339Butyllithium

生成物 1

HCID 540494562-[methyl-N-(methoxycarbonyl)amino]-6-(phenylthio)imidazo[1,2-a]pyridine

試薬・触媒・溶媒 1

HCID 8058Hexane溶媒

実験手順

A suspension of 1.0 g. (0.0033 moles) of 2-(methoxycarbonylamino)-6-(phenylthio) imidazo [1,2-a] pyridine in 35 ml. of tetrahydrofuran under a argon atmosphere is treated dropwise with 1.35 ml. of a 2.45 molar solution of butyllithium in hexane at -20° C. The resultant solution is stirred for 5 minutes and 0.469 g. (0.0033 moles) of methyliodide is added. The reaction mixture is allowed to warm to room temperature and stirred for 30 minutes. The solution is diluted with ice water and the solids are collected by filtration, washed with water and dried. The solid materials is chromatographed on silica gel and eluted with 1:99 methanol in methylene chloride affording 2-[methyl-N-(methoxycarbonyl)amino]-6-(phenylthio) imidazo [1,2-a] pyridine m.p. 147°-149° C.

後処理

  1. additionA suspension of 1.0 g
  2. customat -20° C
  3. filtrationthe solids are collected by filtration
  4. washwashed with water
  5. customdried
  6. customThe solid materials is chromatographed on silica gel
  7. washeluted with 1:99 methanol in methylene chloride

出典と根拠

ORDレコード
ord-cd4a64b056074811b63300e1b3b02414
出典データセット
uspto-grants-1978_06
特許番号
US04096264

反応ノート

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