Sodium Azide → HCID 178440795、化合物

HRID 2253450ノート

反応式

HRID 2253450 の反応式
[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

参加物

6

反応物 3

HCID 33557Sodium AzideHCID 6451240Aluminum(III) ChlorideHCID 53640530HCID 53640530、化合物

生成物 1

HCID 178440795HCID 178440795、化合物収率 70%

試薬・触媒・溶媒 2

HCID 313Hydrochloric Acid溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

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%).

後処理

  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)

出典と根拠

ORDレコード
ord-bd3592927b8746a1a39fcececabd58c2
出典データセット
uspto-grants-2008_01
特許番号
US07323587B2

反応ノート

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