Sodium Azide → HCID 178440795, 화합물

HRID 2253450노트

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HRID 2253450 반응식
[Cl-].[Al+3].[Cl-].[Cl-].[N-:5]=[N+:6]=[N-:7].[Na+].[C:9]1([C:15]([C:25]2[CH:30]=[CH:29][C:28]([CH:31]=[CH:32][C:33]#[N:34])=[CH:27][CH:26]=2)=[C:16]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH2:17][CH3:18])[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1>C1COCC1.Cl>[C:9]1([C:15]([C:25]2[CH:30]=[CH:29][C:28]([CH:31]=[CH:32][C:33]3[NH:34][N:7]=[N:6][N:5]=3)=[CH:27][CH:26]=2)=[C:16]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH2:17][CH3:18])[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1

참가 물질

6

반응물 3

HCID 33557Sodium AzideHCID 6451240Aluminum(III) ChlorideHCID 53640530HCID 53640530, 화합물

생성물 1

HCID 178440795HCID 178440795, 화합물수율 70%

시약·촉매·용매 2

HCID 313Hydrochloric Acid용매HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of aluminum chloride (1.82 g, 13.5 mmol) in THF (20 mL) at 0° C. was added sodium azide (1.77 g, 27 mmol) then nitrile (4b) (888 mg, 2.65 mmol). The mixture was stirred 10 min and heated to reflux. After refluxing overnight the mixture was diluted with 1N HCl, and extracted with EtOAc. The combined organic layers were washed with water, brine and dried (MgSO4). The solvent was removed under reduced pressure and the residue chromatographed (silica gel, 10-20% methanol/CH2Cl2) to give the tetrazole (4c) as a white solid (700 mg, 70%): 1H NMR (CDCl3) δ 7.63 (d, J=16.5 Hz, 1H), 7.39-7.11 (m, 12H), 6.98 (d, J=16.5 Hz, 1H), 6.91 (d, J=8.4 Hz, 2H), 2.48 (q, J=7.3 Hz, 2H), 0.94 (t, J=7.3 Hz, 3H); ESI m/z: 377 (M−H−, 100%).

후처리

  1. temperatureheated to reflux
  2. temperatureAfter refluxing overnight the mixture
  3. extractionextracted with EtOAc
  4. washThe combined organic layers were washed with water, brine
  5. dry with materialdried (MgSO4)
  6. customThe solvent was removed under reduced pressure
  7. customthe residue chromatographed (silica gel, 10-20% methanol/CH2Cl2)

출처 및 근거

ORD 기록
ord-bd3592927b8746a1a39fcececabd58c2
출처 데이터셋
uspto-grants-2008_01
특허 번호
US07323587B2

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