1,2-Dibromoethane → HCID 70593590, compound

HRID 2057377Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[N:9]1[CH:13]=[CH:12][NH:11][C:10]1=[NH:14].[CH2:15](Br)[CH2:16]Br>Cl>[Cl:8][C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([Cl:1])[C:3]=1[N:9]1[C:10]2=[N:14][CH2:15][CH2:16][N:11]2[CH:12]=[CH:13]1

Participants

Conditions

Temperature: 140 °C

Procedure

A mixture consisting of 4.56 gm (0.02 mol) of 1-(2,6-dichloro-phenyl)-2-imino-4-imidazoline and 2.6 ml of ethylene bromide (about 150% of the stoichiometrically required amount) was heated to 140° C. while stirring and was maintained at that temperature for 15 minutes. After cooling, the glassy mass was dissolved in about 1 N hydrochloric acid, and the solution was friactionally extracted with ether at stepwisely increasing pH-values (addition of 2 N sodium hydroxide). Those fractions which contained the reaction product in substantially pure form, as determined by thin-layer chromatography, were combined, dried over anhydrous calcium sulfate and evaporated in vacuo. The residue was further purified by stirring it with acetone and collecting the crystallized product by suction filtration. 0.55 gm (10.8% of theory) of pure 7-(2,6-dichloro-phenyl)-2,3-dihydro-imidazo[1,2-α]imidazole, m.p. 184°-187° C. were obtained.

Workup

temperaturewas maintained at that temperature for 15 minutes
temperatureAfter cooling
extractionthe solution was friactionally extracted with ether at stepwisely increasing pH-values (addition of 2 N sodium hydroxide)
dry with materialdried over anhydrous calcium sulfate
customevaporated in vacuo
customThe residue was further purified
stirringby stirring it with acetone
customcollecting the crystallized product
filtrationby suction filtration

Sources & evidence

ORD record: ord-1c1a1c3741d042c68f62ad43b7361e8c
Source dataset: uspto-grants-1980_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04210659

Reaction notes

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