Sodium Hydroxide → HCID 178477872, compound

HRID 2248902Notes

Reaction equation

[C:1]([C:3]1[O:4][C:5]2[CH:11]=[C:10]([CH2:12][O:13][C:14]3[CH:19]=[CH:18][CH:17]=[C:16](/[CH:20]=[CH:21]/[C:22]4[CH:31]=[CH:30][C:29]5[C:24](=[CH:25][C:26]([Cl:32])=[CH:27][CH:28]=5)[N:23]=4)[CH:15]=3)[CH:9]=[CH:8][C:6]=2[N:7]=1)#[N:2].[N-:33]=[N+:34]=[N-:35].[Na+].[Cl-].[NH4+].[OH-].[Na+]>CN(C=O)C>[Cl:32][C:26]1[CH:25]=[C:24]2[C:29]([CH:30]=[CH:31][C:22](/[CH:21]=[CH:20]/[C:16]3[CH:15]=[C:14]([CH:19]=[CH:18][CH:17]=3)[O:13][CH2:12][C:10]3[CH:9]=[CH:8][C:6]4[N:7]=[C:3]([C:1]5[NH:35][N:34]=[N:33][N:2]=5)[O:4][C:5]=4[CH:11]=3)=[N:23]2)=[CH:28][CH:27]=1

Participants

Conditions

Temperature: 100 °C

Procedure

A solution-suspension of (E)-2-cyano-6-[3-(7-chloro-2-quinolinylethenyl)phenoxymethyl]benzoxazole (950 mg, 2.17 mmol), sodium azide (432.1 mg, 6.51 mmol) and ammonium chloride (348.1 mg, 6.51 mmol) in DMF (15 ml) is heated to 100° C. for 7 hours and stirred at room temperature for 12 hours. The mixture is poured over ice-water and the pH is adjusted to 10 with 1N NaOH. The aqueous mixture is washed with ether and the pH adjusted to 4 with 1N-HCl. The precipitated solid is filtered and washed successively with water, ethanol and methylene chloride. Recrystallization from DMF affords (E)-5-(6-[3-(7-chloro-2-quinolinyl-ethenyl)phenoxymethyl ]benzoxazol-2-yl)tetrazole. (M.P. 272° C. (dec.))

Workup

washThe aqueous mixture is washed with ether
filtrationThe precipitated solid is filtered
washwashed successively with water, ethanol and methylene chloride
customRecrystallization from DMF

Sources & evidence

ORD record: ord-c3da17edc5424cfe9a1fa0609471ae3f
Source dataset: uspto-grants-1991_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05041453

Reaction notes

Loading…