Ammonium Chloride → 6-amino-2,2,7-trifluoro-4-(prop-2-ynyl)-2H-benzo[b][1,4]oxazin-3(4H)-one

HRID 403160노트

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HRID 403160 반응식
[Cl-].[NH4+].[F:3][C:4]1([F:22])[O:9][C:8]2[CH:10]=[C:11]([F:17])[C:12]([N+:14]([O-])=O)=[CH:13][C:7]=2[N:6]([CH2:18][C:19]#[CH:20])[C:5]1=[O:21]>O.CO.O1CCCC1.[Fe]>[NH2:14][C:12]1[C:11]([F:17])=[CH:10][C:8]2[O:9][C:4]([F:3])([F:22])[C:5](=[O:21])[N:6]([CH2:18][C:19]#[CH:20])[C:7]=2[CH:13]=1

참가 물질

6

반응물 2

HCID 25517Ammonium ChlorideHCID 871738852,2,7-trifluoro-6-nitro-4-(prop-2-yn-1-yl)-3,4-dihydro-2H-1,4-benzoxazin-3-one

생성물 1

HCID 866695376-amino-2,2,7-trifluoro-4-(prop-2-ynyl)-2H-benzo[b][1,4]oxazin-3(4H)-one수율 81.5%

시약·촉매·용매 3

HCID 23925Iron촉매HCID 962Water용매HCID 21899815MeOH tetrahydrofuran용매

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온도
70 °C

실험 절차

To ammonium chloride (3.96 g, 74.0 mmol) in water was added iron powder (325 mesh; 4.13 g, 74.0 mmol). To the resulting mixture was added 2,2,7-trifluoro-6-nitro-4-(prop-2-ynyl)-2Hbenzo[b][1,4]oxazin-3(4H)-one (7.06 g, 24.67 mmol) in methanol/tetrahydrofuran. The resulting mixture was stirred vigorously at 70° C. for 2 hours. The reaction was quenched in water/ethyl acetate under stirring. The resulting 2 phase system was filtered and the layers were separated. The water layer was subsequently extracted with ethyl acetate. The combined organic phases were washed with brine, dried with Na2SO4 and concentrated to yield 5.15 g of the title compound. GCMS m/e (M+)=256

후처리

  1. customThe reaction was quenched in water/ethyl acetate
  2. stirringunder stirring
  3. filtrationThe resulting 2 phase system was filtered
  4. customthe layers were separated
  5. extractionThe water layer was subsequently extracted with ethyl acetate
  6. washThe combined organic phases were washed with brine
  7. dry with materialdried with Na2SO4
  8. concentrationconcentrated

출처 및 근거

ORD 기록
ord-da77a239c4c046fcaa4283e31d9723ce
출처 데이터셋
uspto-grants-2014_06
특허 번호
US08748348B2

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