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

HRID 1033016노트

반응식

HRID 1033016 반응식
[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

참가 물질

4

반응물 2

HCID 72352L 696229HCID 87949Lawesson's reagent

생성물 1

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

시약·촉매·용매 1

HCID 1140Toluene용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-4eb1d4fc8a94409f95b7338acb1aa19b
출처 데이터셋
uspto-grants-1994_05
특허 번호
US05308854

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