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

HRID 2065020

반응식

HRID 2065020 반응식
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]

참가 물질

9

반응물 5

HCID 259Bromide ionHCID 947Nitrogen2회HCID 11430Potassium CarbonateHCID 163764-nitro-1H-pyrazoleHCID 10822129Ethyl 4-(chloromethyl)-1,3-thiazole-2-carboxylate

생성물 1

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

시약·촉매·용매 3

HCID 180Acetone용매HCID 962Water용매HCID 8857Ethyl Acetate용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-385828603fc9419ea257798b5641aaa9
출처 데이터셋
uspto-grants-2012_10
특허 번호
US08288419B2

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