Bromine → HCID 178419605, compound

HRID 1413443Notes

Reaction equation

HRID 1413443 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]=[C:9]2[NH:13][CH2:12][CH2:11][NH:10]2)=[CH:4][CH:3]=1.[Br:14]Br>C(Cl)(Cl)Cl>[BrH:14].[Br:14][C:7]1[CH:6]=[C:5]([N:8]=[C:9]2[NH:10][CH2:11][CH2:12][NH:13]2)[CH:4]=[CH:3][C:2]=1[F:1]

Participants

4

Reactant 2

HCID 24408BromineHCID 178505866HCID 178505866, compound

Product 1

HCID 178419605HCID 178419605, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

10.75 gm (0.06 mol) of 2-(4-fluoro-phenylimino)-imidazolidine base were dissolved in 210 ml of chloroform, and the solution was dropwisely admixed with bromine at 10° C. while thoroughly stirring. A solid substance precipitated. The mixture was stirred for 30 minutes at 10° C., then suction-filtered, and the filter cake was thoroughly washed with ether and dried, yielding raw 2-(3-bromo-4-fluoro-phenyl-imino)-imidazolidine hydrobromide, m.p. 137°-139° C. The raw hydrobromide was dissolved in water, and the solution was fractionally extracted with ether at gradually increasing pH-values (stepwise alkalization with 2 N sodium hydroxide). The thin layer-chromatographically uniform ether extracts were combined, dried over magnesium sulfate, filtered and acidified with ethereal hydrochloric acid until acid to Congo red. A white substance separated out, which was collected by suction filtration, washed with ether and dried. Yield: 4.12 gm (23.3% of theory) of the hydrochloride, m.p. 182.5° C., Rf -value 0.7 in mobile phase 50 parts benzene, 40 parts dioxane, 5 parts concentrated ammonia, 5 parts ethanol. Carrier: silicagel with fluorescent pigment ZS; visualization; ultraviolet light and potassium platinate.

Workup

  1. customA solid substance precipitated
  2. stirringThe mixture was stirred for 30 minutes at 10° C.
  3. filtrationsuction-filtered
  4. washthe filter cake was thoroughly washed with ether
  5. customdried

Sources & evidence

ORD record
ord-64b3c787a9e947e5b46db1e9d2382417
Source dataset
uspto-grants-1981_02
Patent number
US04250186

Reaction notes

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