Nitrogen → HCID 67365635, 화합물

HRID 42819노트

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HRID 42819 반응식
N#N.Cl[CH2:4][C:5]1[O:9][N:8]=[C:7]([C:10](=[O:12])[CH3:11])[CH:6]=1.[N+:13]([C:16]1[CH:20]=[N:19][NH:18][N:17]=1)([O-:15])=[O:14].CCN(C(C)C)C(C)C>CN(C=O)C.CC(=O)OCC.O>[N+:13]([C:16]1[CH:20]=[N:19][N:18]([CH2:4][C:5]2[O:9][N:8]=[C:7]([C:10](=[O:12])[CH3:11])[CH:6]=2)[N:17]=1)([O-:15])=[O:14]

참가 물질

8

반응물 4

HCID 947NitrogenHCID 81531DiisopropylethylamineHCID 2781504-nitro-2H-1,2,3-triazoleHCID 132967023-Acetyl-5-chloromethylisoxazole

생성물 1

HCID 67365635HCID 67365635, 화합물

시약·촉매·용매 3

HCID 962Water용매HCID 6228Dimethylformamide용매2회HCID 8857Ethyl Acetate용매

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온도
50 °C

실험 절차

In a flame dried round-bottomed flask equipped with a magnetic stir bar and under inert atmosphere (N2), a solution of 1-(5-hydroxymethyl-isoxazol-3-yl)-ethanone (262 mg, 1.86 mmol) in dry CH2Cl2 (2.6 mL) was treated at 0° C. with Et3N (0.34 mL, 2.41 mmol) followed by DMAP (23 mg, 0.19 mmol) and Ms-Cl (0.17 mL, 2.23 mmol). After stirring at rt for 2 h, the reaction mixture was quenched with water (10 mL), extracted with CH2Cl2 (2×10 mL) and the combined org. extracts were dried over NaSO4, filtered, and the solvents were removed under reduced pressure to give crude 1-(5-chloromethyl-isoxazol-3-yl)-ethanone as a pale yellow oil. In a flame dried round-bottomed flask equipped with a magnetic stir bar and under inert atmosphere (N2), a solution of this crude 1-(5-chloromethyl-isoxazol-3-yl)-ethanone in DMF (3.0 mL) was added to a solution of 4-nitro-2H-[1,2,3]triazole (210 mg, 1.84 mmol) in DMF (3.0 mL) pre-treated for 30 min with DIPEA (0.63 mL, 3.68 mmol) and the reaction mixture was stirred for 16 h at 50° C. Water (10 mL), followed by EA (10 mL) were added. The aq. layer was extracted with EA (10 mL) and the combined org. extracts were dried over NaSO4, filtered, and the solvents were removed under reduced pressure. Purification of the residue by FC (2:1 hept-EA) gave the title compound as a pale yellow oil: TLC:rf (2:1 hept-EA)=0.26. LC-MS-conditions 02: tR=0.90 min.

후처리

  1. additionwere added
  2. extractionThe aq. layer was extracted with EA (10 mL)
  3. dry with materialextracts were dried over NaSO4
  4. filtrationfiltered
  5. customthe solvents were removed under reduced pressure
  6. customPurification of the residue by FC (2:1 hept-EA)

출처 및 근거

ORD 기록
ord-ac4edb4533d14db7a3322c91810af85a
출처 데이터셋
uspto-grants-2013_09
특허 번호
US08536209B2

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