L 696229 → 3-[2-(1,3-benzoxazol-2-yl)ethyl]-5-ethyl-6-methyl-1H-pyridine-2-thione

HRID 1033016ノート

反応式

HRID 1033016 の反応式
[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[CH2:10][CH2:11][C:12]1[C:13](=O)[NH:14][C:15]([CH3:20])=[C:16]([CH2:18][CH3:19])[CH:17]=1.COC1C=CC(P2(=S)SP(=S)(C3C=CC(OC)=CC=3)[S:31]2)=CC=1>C1(C)C=CC=CC=1>[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[CH2:10][CH2:11][C:12]1[C:13](=[S:31])[NH:14][C:15]([CH3:20])=[C:16]([CH2:18][CH3:19])[CH:17]=1

参加物

4

反応物 2

HCID 72352L 696229HCID 87949Lawesson's reagent

生成物 1

HCID 30004373-[2-(1,3-benzoxazol-2-yl)ethyl]-5-ethyl-6-methyl-1H-pyridine-2-thione収率 24.7%

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

実験手順

A mixture of 3-[2-(benzoxazol-2-yl)-ethyl]-5-ethyl-6-methyl pyridin-2(1H)-one (150 mg, 0.53 mmol) and 2,4-bis(4-methoxyphenyl)-1,3-dithia-2,4-diphosphetane-2,4-disulfide (Lawesson's Reagent) (485 mg, 1.2 mmol) in dry toluene (4 mL) was refluxed for 6-10 hours. The solvent was evaporated and the reaction residue was flash chromatographed on silica gel eluting with 0.5% methanol/chloroform. The appropriate fractions were combined and crystallized from ethyl acetate to yield 80 mg of slightly impure product. This material was re-chromatographed on silica gel eluting with chloroform. The appropriate fractions were combined, the solvent evaporated, and the residue recrystallized from boiling diethyl ether, after addition of sufficient methylene chloride to effect complete dissolution, to yield 39 mg (24%) of pure product, m.p. 199°-201° C.

後処理

  1. temperaturewas refluxed for 6-10 hours
  2. customThe solvent was evaporated
  3. customchromatographed on silica gel eluting with 0.5% methanol/chloroform
  4. customcrystallized from ethyl acetate
  5. customto yield 80 mg of slightly impure product
  6. customThis material was re-chromatographed on silica gel eluting with chloroform
  7. customthe solvent evaporated
  8. customthe residue recrystallized
  9. additionafter addition of sufficient methylene chloride
  10. dissolutiondissolution

出典と根拠

ORDレコード
ord-4eb1d4fc8a94409f95b7338acb1aa19b
出典データセット
uspto-grants-1994_05
特許番号
US05308854

反応ノート

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