Thionyl Chloride → 5,6-difluoro-2,4-dihydro-1H-3,1-benzoxazine-2,4-dione

HRID 1378008노트

반응식

HRID 1378008 반응식
S(Cl)(Cl)=O.C([O:9][C:10]([NH:12][C:13]1[CH:21]=[CH:20][C:19]([F:22])=[C:18]([F:23])[C:14]=1[C:15]([OH:17])=[O:16])=O)(C)(C)C>O1CCCC1>[F:23][C:18]1[C:14]2[C:15](=[O:17])[O:16][C:10](=[O:9])[NH:12][C:13]=2[CH:21]=[CH:20][C:19]=1[F:22]

참가 물질

4

반응물 2

HCID 24386Thionyl ChlorideHCID 229144216-((tert-Butoxycarbonyl)amino)-2,3-difluorobenzoic acid

생성물 1

HCID 229144245,6-difluoro-2,4-dihydro-1H-3,1-benzoxazine-2,4-dione수율 77.5%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

A solution of 108 ml of thionyl chloride in 300 ml of tetrahydrofuran was added dropwise while cooling with ice to a solution of 100 g (366 mmol) of 2-(tert.-butoxycarbonyl)amino-5,6-difluorobenzoic acid in 1.5 I of dry tetrahydrofuran, whereupon the mixture was stirred at room temperature for 16 hours. The brown solution was evaporated and the brown solid obtained was triturated with methylene chloride. The beige powder obtained was filtered off and dried in a high vacuum. There were obtained 56.5 g (77%) of 5,6-difluoro-2,4-dihydro-1H-3,1-benzoxazine-2,4-dione as a beige powder of m.p. >240°.

후처리

  1. customThe brown solution was evaporated
  2. customthe brown solid obtained
  3. customwas triturated with methylene chloride
  4. customThe beige powder obtained
  5. filtrationwas filtered off
  6. customdried in a high vacuum

출처 및 근거

ORD 기록
ord-67f724e6c1e6457ebc0811b18188936c
출처 데이터셋
uspto-grants-1997_09
특허 번호
US05665718

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