Bromide ion → 4-(4-Nitro-pyrazol-1-ylmethyl)-thiazole-2-carboxylic acid ethyl ester

HRID 2065020

反応式

HRID 2065020 の反応式
N#N.[CH2:3]([O:5][C:6]([C:8]1[S:9][CH:10]=[C:11]([CH2:13]Cl)[N:12]=1)=[O:7])[CH3:4].C([O-])([O-])=O.[K+].[K+].[N+:21]([C:24]1[CH:25]=[N:26][NH:27][CH:28]=1)([O-:23])=[O:22].[Br-]>CC(C)=O.CC(=O)OCC.O>[CH2:3]([O:5][C:6]([C:8]1[S:9][CH:10]=[C:11]([CH2:13][N:26]2[CH:25]=[C:24]([N+:21]([O-:23])=[O:22])[CH:28]=[N:27]2)[N:12]=1)=[O:7])[CH3:4]

参加物

9

反応物 5

HCID 259Bromide ionHCID 947Nitrogen2 回HCID 11430Potassium CarbonateHCID 163764-nitro-1H-pyrazoleHCID 10822129Ethyl 4-(chloromethyl)-1,3-thiazole-2-carboxylate

生成物 1

HCID 669288954-(4-Nitro-pyrazol-1-ylmethyl)-thiazole-2-carboxylic acid ethyl ester

試薬・触媒・溶媒 3

HCID 180Acetone溶媒HCID 962Water溶媒HCID 8857Ethyl Acetate溶媒

実験手順

In a flame dried round-bottomed flask equipped with a magnetic stir bar and under inert atmosphere (N2), a solution of 4-chloromethyl-thiazole-2-carboxylic acid ethyl ester (1.84 g, 8.93 mmol) in acetone (20.0 mL) was treated, under inert atmosphere (N2) with K2CO3 (6.23 g, 44.66 mmol) followed by 4-nitro-1H-pyrazole (1.00 g, 8.93 mmol) and TBA bromide (576 mg, 1.79 mmol). The resulting mixture was stirred at rt overnight. Water (40 mL), followed by EA (50 mL) were added. The aq. layer was extracted with EA (50 mL) and the combined org. extracts were dried over MgSO4, filtered, and the solvents were removed under reduced pressure. Purification of the residue by FC (50:50 hept-EA) gave the title compound as a yellow oil. TLC: rf (50:50 hept-EA)=0.30. LC-MS-conditions 02: tR=0.90 min; [M+H]+=283.25.

後処理

  1. additionwere added
  2. extractionThe aq. layer was extracted with EA (50 mL)
  3. dry with materialextracts were dried over MgSO4
  4. filtrationfiltered
  5. customthe solvents were removed under reduced pressure
  6. customPurification of the residue by FC (50:50 hept-EA)

出典と根拠

ORDレコード
ord-385828603fc9419ea257798b5641aaa9
出典データセット
uspto-grants-2012_10
特許番号
US08288419B2

関連ノート

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