Diethyl Ether → 9-Bromo-2-[1,3,4]oxadiazol-2-yl-4,5-dihydro-6-oxa-3-thia-1-aza-benzo[e]azulene

HRID 628064Notes

Reaction equation

[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[O:14][CH2:13][CH2:12][C:11]3[S:10][C:9]([C:15]([NH:17][NH2:18])=[O:16])=[N:8][C:7]=3[C:6]=2[CH:19]=1.[C:20]1(C)C=CC(S(O)(=O)=O)=CC=1.C(OCC)C>C(OC)(OC)OC>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[O:14][CH2:13][CH2:12][C:11]3[S:10][C:9]([C:15]4[O:16][CH:20]=[N:18][N:17]=4)=[N:8][C:7]=3[C:6]=2[CH:19]=1

Participants

Conditions

Temperature: 100 °C

Procedure

To a solution of 9-bromo-4,5-dihydro-6-oxa-3-thia-1-aza-benzo[e]azulene-2-carboxylic acid hydrazide (400 mg) in trimethyl orthoformate (10 mL) was added p-toluenesulfonic acid (100 mg) and the reaction heated at 100° C. for 16 h. After cooling to room temperature, the solvent was reduced in vacuo and diethyl ether (10 mL) was added. The resulting solid was filtered and air-dried to give 9-bromo-2-[1,3,4]oxadiazol-2-yl-4,5-dihydro-6-oxa-3-thia-1-aza-benzo[e]azulene.

Workup

temperatureAfter cooling to room temperature
additionwas added
filtrationThe resulting solid was filtered
customair-dried

Sources & evidence

ORD record: ord-84c8c49319a845ca93b45266f060af3e
Source dataset: uspto-grants-2016_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09309265B2

Reaction notes

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