Triethylamine → (Z)-N-[5-Fluoro-2-methyl-1-(4-methylthiobenzylidene)inden-3-ylmethyl]-N'-hydroxy-N'-methyl urea

HRID 379629노트

반응식

HRID 379629 반응식
Cl.[CH3:2][NH:3][OH:4].C(N(CC)CC)C.[F:12][C:13]1[CH:14]=[C:15]2[C:19](=[CH:20][CH:21]=1)/[C:18](=[CH:22]\[C:23]1[CH:28]=[CH:27][C:26]([S:29][CH3:30])=[CH:25][CH:24]=1)/[C:17]([CH3:31])=[C:16]2[CH2:32][N:33]=[C:34]=[O:35]>C1COCC1>[F:12][C:13]1[CH:14]=[C:15]2[C:19](=[CH:20][CH:21]=1)/[C:18](=[CH:22]\[C:23]1[CH:28]=[CH:27][C:26]([S:29][CH3:30])=[CH:25][CH:24]=1)/[C:17]([CH3:31])=[C:16]2[CH2:32][NH:33][C:34]([N:3]([OH:4])[CH3:2])=[O:35]

참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 77906N-methylhydroxylamine hydrochlorideHCID 86745524(Z)-5-Fluoro-2-methyl-1-(4-methylthiobenzylidene)inden-3-ylmethyl isocyanate

생성물 1

HCID 10134627(Z)-N-[5-Fluoro-2-methyl-1-(4-methylthiobenzylidene)inden-3-ylmethyl]-N'-hydroxy-N'-methyl urea

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

To a suspension of N-methyl hydroxylamine hydrochloride (9.82 g, 117.6 mmol) in THF (150 mL) at room temperature there was added triethylamine (16.3 mL, 117.6 mmol) and the mixture stirred for 10 minutes. There was added, over 15 minutes, a solution of the isocyanate from Step 1 in THF (100 mL). After 2 hours of stirring at room temperature, the THF was evaporated and the residue, on trituration with water, afforded a yellow solid which was filtered. This solid was stirred in ether (150 mL) and filtered again. This crude material was chromatographed on silica gel eluting with 5% ethanol in methylene chloride. The more polar component of the mixture was stirred with methylene chloride (50 mL) for 2 hours and filtered and the solid crystallized from ethyl acetate to afford the pure title product as yellow crystals, mp 190-192° C. dec.

후처리

  1. additionThere was added, over 15 minutes
  2. stirringAfter 2 hours of stirring at room temperature
  3. customthe THF was evaporated
  4. customthe residue, on trituration with water, afforded a yellow solid which
  5. filtrationwas filtered
  6. stirringThis solid was stirred in ether (150 mL)
  7. filtrationfiltered again
  8. customThis crude material was chromatographed on silica gel eluting with 5% ethanol in methylene chloride
  9. stirringThe more polar component of the mixture was stirred with methylene chloride (50 mL) for 2 hours
  10. filtrationfiltered
  11. customthe solid crystallized from ethyl acetate

출처 및 근거

ORD 기록
ord-bafbf715b56b4c879245a33f5bc4a8b8
출처 데이터셋
uspto-grants-2001_10
특허 번호
US06300346B1

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