Nitrogen → HCID 67957872, 화합물

HRID 82811

반응식

HRID 82811 반응식
N#N.Cl[CH2:4][C:5]1[N:6]=[C:7]([C:10]([O:12][CH2:13][CH3:14])=[O:11])[S:8][CH:9]=1.[N+:15]([C:18]1[CH:22]=[N:21][NH:20][N:19]=1)([O-:17])=[O:16].CCN(C(C)C)C(C)C>CN(C=O)C.CC(=O)OCC.O>[N+:15]([C:18]1[CH:22]=[N:21][N:20]([CH2:4][C:5]2[N:6]=[C:7]([C:10]([O:12][CH2:13][CH3:14])=[O:11])[S:8][CH:9]=2)[N:19]=1)([O-:17])=[O:16]

참가 물질

8

반응물 4

HCID 947NitrogenHCID 81531DiisopropylethylamineHCID 2781504-nitro-2H-1,2,3-triazoleHCID 10822129Ethyl 4-(chloromethyl)-1,3-thiazole-2-carboxylate

생성물 1

HCID 67957872HCID 67957872, 화합물

시약·촉매·용매 3

HCID 962Water용매HCID 6228Dimethylformamide용매3회HCID 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 ethyl 4-(chloromethyl)thiazole-2-carboxylate (WO 2009077990 A1) (2.16 g, 10.5 mmol) in DMF (15.0 mL) was added to a solution of 4-nitro-2H-[1,2,3]triazole (T. E. Eagles et al. Organic preparations and procedures 2 (2), 117-119, 1970; P. N. Neuman J. Heterocycl. Chem. 8, 51-56, 1971) (8.0 g of a 10% solution in DMF, 7.01 mmol) in DMF (15.0 mL) pre-treated for 30 min with DIPEA (1.82 mL, 2.33 mmol) and the reaction mixture was stirred overnight at 50° C. Water (50 mL), followed by EA (50 mL) was added. The layers were separated and the aq. layer was washed with water (50 mL), dried over MgSO4, filtered, and the solvents were removed under reduced pressure. Purification of the residue by FC (60:40 hept-EA)) gave the title compound as a yellow oil. TLC: rf (7:3 hept-EA)=0.36. LC-MS-conditions 07: tR=0.76 min, [M+H]+=284.28.

후처리

  1. additionwas added
  2. customThe layers were separated
  3. washthe aq. layer was washed with water (50 mL)
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customthe solvents were removed under reduced pressure
  7. customPurification of the residue by FC (60:40 hept-EA))

출처 및 근거

ORD 기록
ord-98a13a8e4c63474f8817f5edd0f5d2f2
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08846733B2

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