Nitrogen → 1-[2-(4-Nitro-[1,2,3]triazol-2-ylmethyl)-oxazol-4-yl]-ethanone

HRID 42855

반응식

HRID 42855 반응식
N#N.[C:3]([C:6]1[N:7]=[C:8]([CH2:11]OS(C)(=O)=O)[O:9][CH:10]=1)(=[O:5])[CH3:4].[N+:17]([C:20]1[CH:24]=[N:23][NH:22][N:21]=1)([O-:19])=[O:18].CCN(C(C)C)C(C)C>CN(C=O)C.CC(=O)OCC.O>[N+:17]([C:20]1[CH:24]=[N:23][N:22]([CH2:11][C:8]2[O:9][CH:10]=[C:6]([C:3](=[O:5])[CH3:4])[N:7]=2)[N:21]=1)([O-:19])=[O:18]

참가 물질

8

반응물 4

HCID 947NitrogenHCID 81531DiisopropylethylamineHCID 2781504-nitro-2H-1,2,3-triazoleHCID 86649491Methanesulfonic acid 4-acetyl-oxazol-2-ylmethyl ester

생성물 1

HCID 671277401-[2-(4-Nitro-[1,2,3]triazol-2-ylmethyl)-oxazol-4-yl]-ethanone

시약·촉매·용매 3

HCID 962Water용매HCID 6228Dimethylformamide용매2회HCID 8857Ethyl Acetate용매

반응 조건

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 methanesulfonic acid 4-acetyl-oxazol-2-ylmethyl ester (116 mg, 0.53 mmol) in DMF (3.0 mL) was added to a solution of 4-nitro-2H-[1,2,3]triazole (62 mg, 0.53 mmol) in DMF (2.0 mL) pre-treated for 30 min with DIPEA (0.20 mL, 1.17 mmol) and the reaction mixture was stirred for 20 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 (3:1 to 1:1 hept-EA) gave the title compound as a yellow solid. TLC:rf (1:2 hept-EA)=0.49. LC-MS-conditions 01: tR=0.76 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 (3:1 to 1:1 hept-EA)

출처 및 근거

ORD 기록
ord-35d322c817cd48fd88f5b12a53bd2795
출처 데이터셋
uspto-grants-2013_09
특허 번호
US08536209B2

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