Bromide ion → 2-(2-Methyl-[1,3]dioxolan-2-yl)-4-(3-nitro-pyrazol-1-ylmethyl)-thiazole

HRID 2065038ノート

反応式

HRID 2065038 の反応式
N#N.Cl[CH2:4][C:5]1[N:6]=[C:7]([C:10]2([CH3:15])[O:14][CH2:13][CH2:12][O:11]2)[S:8][CH:9]=1.[N+:16]([C:19]1[NH:23][N:22]=[CH:21][CH:20]=1)([O-:18])=[O:17].C([O-])([O-])=O.[K+].[K+].[Br-]>CC(C)=O.CC(=O)OCC.O>[CH3:15][C:10]1([C:7]2[S:8][CH:9]=[C:5]([CH2:4][N:22]3[CH:21]=[CH:20][C:19]([N+:16]([O-:18])=[O:17])=[N:23]3)[N:6]=2)[O:14][CH2:13][CH2:12][O:11]1

参加物

9

反応物 5

HCID 259Bromide ionHCID 947NitrogenHCID 11430Potassium CarbonateHCID 1234193-NitropyrazoleHCID 669288134-Chloromethyl-2-(2-methyl-[1,3]dioxolan-2-yl)-thiazole

生成物 1

HCID 669292022-(2-Methyl-[1,3]dioxolan-2-yl)-4-(3-nitro-pyrazol-1-ylmethyl)-thiazole

試薬・触媒・溶媒 3

HCID 180Acetone溶媒2 回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-2-(2-methyl-[1,3]dioxolan-2-yl)-thiazole (174 mg, 0.79 mmol) in acetone (2.0 mL) was added to a solution of 5-nitro-1H-pyrazole (90 mg, 0.79 mmol) in acetone (2.0 mL). K2CO3 (330 mg, 2.38 mmol) followed by TBA bromide (51 mg, 0.16 mmol) were added and the reaction mixture was stirred at rt overnight. Water (10 mL) and EA (10 mL) were added. The aq. layer was extracted with EA (10 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 (1:1 hept-EA) gave the title compound as a pale yellow oil. TLC: rf (1:1 hept-EA)=0.29. LC-MS-conditions 02: tR=0.89 min, [M+H]+=297.23.

後処理

  1. additionwere added
  2. extractionThe aq. layer was extracted with EA (10 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 (1:1 hept-EA)

出典と根拠

ORDレコード
ord-847dc52d889d4f81ac88a42543f6fa0e
出典データセット
uspto-grants-2012_10
特許番号
US08288419B2

反応ノート

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