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

HRID 403159ノート

反応式

HRID 403159 の反応式
[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]

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 25517Ammonium Chloride溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-d1a3074d518b49589435e8b0b2057f3e
出典データセット
uspto-grants-2014_06
特許番号
US08748348B2

反応ノート

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