Nitrogen → 2-[2-(2-Methyl-[1,3]dioxolan-2-yl)-thiazol-4-ylmethyl]-4-nitro-2H-[1,2,3]triazole

HRID 42798

반응식

HRID 42798 반응식
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[CH:23]=[N:22][NH:21][N:20]=1)([O-:18])=[O:17].CCN(C(C)C)C(C)C>CN(C=O)C.CC(=O)OCC.O>[CH3:15][C:10]1([C:7]2[S:8][CH:9]=[C:5]([CH2:4][N:21]3[N:20]=[C:19]([N+:16]([O-:18])=[O:17])[CH:23]=[N:22]3)[N:6]=2)[O:14][CH2:13][CH2:12][O:11]1

참가 물질

8

반응물 4

HCID 947NitrogenHCID 81531DiisopropylethylamineHCID 2781504-nitro-2H-1,2,3-triazoleHCID 669288134-Chloromethyl-2-(2-methyl-[1,3]dioxolan-2-yl)-thiazole

생성물 1

HCID 673658652-[2-(2-Methyl-[1,3]dioxolan-2-yl)-thiazol-4-ylmethyl]-4-nitro-2H-[1,2,3]triazole

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 4-chloromethyl-2-(2-methyl-[1,3]dioxolan-2-yl)-thiazole (231 mg, 1.05 mmol) in DMF (1.5 mL) was added to a solution of 4-nitro-2H-[1,2,3]triazole (100 mg, 0.88 mmol) in DMF (1.5 mL) pre-treated for 30 min with DIPEA (0.30 mL, 1.75 mmol) and the reaction mixture was stirred for 48 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 (6:4 hept-EA) gave the title compound as a pale yellow oil: TLC:rf (6:4 hept-EA)=0.33. LC-MS-conditions 02: tR=0.90 min, [M+H]+=298.23.

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 (6:4 hept-EA)

출처 및 근거

ORD 기록
ord-f88ec056013e4030b1a4a71625adc1de
출처 데이터셋
uspto-grants-2013_09
특허 번호
US08536209B2

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