Dimethylformamide → 5-(6-(3-(Quinolin-2-ylmethyloxy)benzyloxy)benzoxazol-2-yl)tetrazole

HRID 2248881Notes

Reaction equation

[C:1]([C:3]1[O:4][C:5]2[CH:11]=[C:10]([O:12][CH2:13][C:14]3[CH:19]=[CH:18][CH:17]=[C:16]([O:20][CH2:21][C:22]4[CH:31]=[CH:30][C:29]5[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=5)[N:23]=4)[CH:15]=3)[CH:9]=[CH:8][C:6]=2[N:7]=1)#[N:2].[N-:32]=[N+:33]=[N-:34].[Na+].Cl.N1C=CC=CC=1.CN(C)C=O>O>[N:23]1[C:24]2[C:29](=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH:30]=[CH:31][C:22]=1[CH2:21][O:20][C:16]1[CH:15]=[C:14]([CH:19]=[CH:18][CH:17]=1)[CH2:13][O:12][C:10]1[CH:9]=[CH:8][C:6]2[N:7]=[C:3]([C:1]3[NH:34][N:33]=[N:32][N:2]=3)[O:4][C:5]=2[CH:11]=1

Participants

Conditions

Temperature: 100 °C

Procedure

2-cyano-6-(3-(quinolin-2-ylmethyloxy)benzyloxy)benzoxazole (2.97 mmoles), sodium azide (965 mg), pyridine hydrochloride (1.72 g) and dimethylformamide (7 ml) are combined and heated at 100° C. for 48 hours. The reaction mixture is poured into cold water and the resulting precipitate is collected. The precipitate is dissolved in hot ethanol and reprecipitated by addition of water to give 5-(6-(3-(quinolin-2-ylmethyloxy)benzyloxy)benzoxazol-2-yl)tetrazole.

Workup

customthe resulting precipitate is collected
dissolutionThe precipitate is dissolved in hot ethanol
customreprecipitated by addition of water

Sources & evidence

ORD record: ord-03fa24cc9aa54573a7b87be4773ef41b
Source dataset: uspto-grants-1991_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05041453

Reaction notes

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