Propargyl bromide → 2,2,7-trifluoro-6-nitro-4-(prop-2-yn-1-yl)-3,4-dihydro-2H-1,4-benzoxazin-3-one

HRID 403159노트

반응식

HRID 403159 반응식
[F:1][C:2]1([F:17])[O:7][C:6]2[CH:8]=[C:9]([F:15])[C:10]([N+:12]([O-:14])=[O:13])=[CH:11][C:5]=2[NH:4][C:3]1=[O:16].C(=O)([O-])[O-].[K+].[K+].Br[CH2:25][C:26]#[CH:27]>CN(C)C=O.[NH4+].[Cl-]>[F:17][C:2]1([F:1])[O:7][C:6]2[CH:8]=[C:9]([F:15])[C:10]([N+:12]([O-:14])=[O:13])=[CH:11][C:5]=2[N:4]([CH2:27][C:26]#[CH:25])[C:3]1=[O:16]

참가 물질

6

반응물 3

HCID 7842Propargyl bromideHCID 11430Potassium CarbonateHCID 668358542,2,7-trifluoro-6-nitro-2H-benzo[b][1,4]oxazin-3(4H)-one

생성물 1

HCID 871738852,2,7-trifluoro-6-nitro-4-(prop-2-yn-1-yl)-3,4-dihydro-2H-1,4-benzoxazin-3-one수율 88.7%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 25517Ammonium Chloride용매

실험 절차

To 2,2,7-trifluoro-6-nitro-2H-benzo[b][1,4]oxazin-3(4H)-one (6.9 g, 27.8 mmol) and potassium carbonate (4.61 g, 33.4 mmol) in dry N,N-dimethylformamide at RT was dropwise added 3-bromoprop-1-yne (80 wt % in toluene; 4.96 g, 33.4 mmol). The resulting mixture was stirred at RT overnight. The reaction mixture was poured in saturated aqueous NH4Cl solution and extracted with ethyl acetate. The combined extracts were washed with aqueous NaCl solution, dried with Na2SO4, concentrated and chased with toluene to yield 7.06 g of the title compound as dark brown solid.

후처리

  1. customat RT
  2. extractionextracted with ethyl acetate
  3. washThe combined extracts were washed with aqueous NaCl solution
  4. dry with materialdried with Na2SO4
  5. concentrationconcentrated

출처 및 근거

ORD 기록
ord-d1a3074d518b49589435e8b0b2057f3e
출처 데이터셋
uspto-grants-2014_06
특허 번호
US08748348B2

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