Ethyl isocyanate → (+/-)-1-Ethyl-3-[6-fluoro-2,3-dihydro-2',4'-dioxospiro[4H-1-benzopyran-4,5'-thiazolidin]-8-yl]-urea

HRID 279880노트

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HRID 279880 반응식
[NH2:1][C:2]1[C:7]2[O:8][CH2:9][CH2:10][C:11]3([S:15][C:14](=[O:16])[NH:13][C:12]3=[O:17])[C:6]=2[CH:5]=[C:4]([F:18])[CH:3]=1.[CH2:19]([N:21]=[C:22]=[O:23])[CH3:20]>O1CCCC1>[CH2:19]([NH:21][C:22]([NH:1][C:2]1[C:7]2[O:8][CH2:9][CH2:10][C:11]3([S:15][C:14](=[O:16])[NH:13][C:12]3=[O:17])[C:6]=2[CH:5]=[C:4]([F:18])[CH:3]=1)=[O:23])[CH3:20]

참가 물질

4

반응물 2

HCID 8022Ethyl isocyanateHCID 13998518(+/-)-6-Fluoro-8-amino-2,3-dihydrospiro[4H-1-benzopyran-4,5'-thiazolidine]-2',4'-dione

생성물 1

HCID 13998530(+/-)-1-Ethyl-3-[6-fluoro-2,3-dihydro-2',4'-dioxospiro[4H-1-benzopyran-4,5'-thiazolidin]-8-yl]-urea

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

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온도
50 °C

실험 절차

268 mg of (±)-8-amino-6-fluoro-2,3-dihydrospiro[4H-1-benzopyran-4,5'-thiazolidine]-2',4'-dione were stirred in 2 ml of tetrahydrofuran with 100 μl of ethyl isocyanate at room temperature for 2.5 hours and the mixture was subsequently heated to 50° C. for an additional 2 hours. The liquid constituents were removed under reduced pressure, he residue was purified by chromatography on a silica gel column using hexane/ethyl acetate (1:2) for the elution, decolorized with active carbon and recrystallized from ethyl acetate/hexane. (±)-1-Ethyl-3-[6-fluoro-2,3-dihydro-2',4'-dioxospiro[4H-1-benzopyran-4,5'-thiazolidin]-8-yl]-urea was obtained in the form of colorless crystals of melting point 197°-199° C.

후처리

  1. customThe liquid constituents were removed under reduced pressure, he residue
  2. customwas purified by chromatography on a silica gel column
  3. washfor the elution
  4. customrecrystallized from ethyl acetate/hexane

출처 및 근거

ORD 기록
ord-4ddaf572402346b5a5d91e7e729c3ca7
출처 데이터셋
uspto-grants-1986_05
특허 번호
US04587256

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