Methanol → HCID 20032352, 화합물

HRID 231432노트

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HRID 231432 반응식
[Cl:1][C:2]1[C:7](CO)=[CH:6][C:5]([N:10]2[C:14](=[O:15])[C:13]3[CH2:16][CH2:17][CH2:18][CH2:19][C:12]=3[C:11]2=[O:20])=[C:4]([F:21])[CH:3]=1.[C:22]1([N:28]=[C:29]=[O:30])[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.C(N(CC)CC)C.C[OH:39]>C(OCC)(=O)C>[Cl:1][C:2]1[C:7]([O:30][C:29]([NH:28][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[O:39])=[CH:6][C:5]([N:10]2[C:14](=[O:15])[C:13]3[CH2:16][CH2:17][CH2:18][CH2:19][C:12]=3[C:11]2=[O:20])=[C:4]([F:21])[CH:3]=1

참가 물질

6

반응물 4

HCID 887MethanolHCID 7672Phenyl isocyanate2회HCID 8471TriethylamineHCID 13629754N-(4-chloro-2-fluoro-5-hydroxymethylphenyl)-3,4,5,6-tetrahydrophthalimide

생성물 1

HCID 20032352HCID 20032352, 화합물

시약·촉매·용매 1

HCID 8857Ethyl Acetate용매

실험 절차

A mixture of 0.5 g (0.0016 mole) of N-(4-chloro-2-fluoro-5-hydroxymethylphenyl]-3,4,5,6-tetrahydrophthalimide, 0.66 g (0.0055 mole) of phenyl isocyanate, 0.73 g (0.0072 mole) of triethylamine, and 25 ml of methylene was stirred at room temperature overnight. Sufficient methanol was added to react with the excess phenyl isocyanate, and the reaction mixture was stirred for an additional 24 hours. The reaction mixture was diluted with ethyl acetate and was washed successively with water and 5% hydrochloric acid. The organic phase was dried, filtered, and the solvent was evaporated under reduced pressure. The residue was passed through a column of silica gel. The appropriate fractions were combined, and the solvent was evaporated under reduced pressure, leaving a white solid as a residue. This solid was recrystallized from ethyl acetate/heptane, yielding 0.29 g of N-[4-chloro-2-fluoro-5-(phenylaminocarbonyloxy)phenyl]-3,4,5,6-tetrahydrophthalimide as a white solid, m.p. 149°-151° C. The nmr and ir spectra were consistent with the proposed structure.

후처리

  1. stirringthe reaction mixture was stirred for an additional 24 hours
  2. washwas washed successively with water and 5% hydrochloric acid
  3. customThe organic phase was dried
  4. filtrationfiltered
  5. customthe solvent was evaporated under reduced pressure
  6. customthe solvent was evaporated under reduced pressure
  7. customleaving a white solid as a residue
  8. customThis solid was recrystallized from ethyl acetate/heptane

출처 및 근거

ORD 기록
ord-afeb54faef7449ceaa56a1c6621796f7
출처 데이터셋
uspto-grants-1989_07
특허 번호
US04846882

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