Bromine → 3'-Bromo-2',3'-dihydro-2H,5H-spiro[imidazolidine-4,1'-indene]-2,5-dione

HRID 637314Notes

Reaction equation

HRID 637314 reaction equation
[C:1]12([C:13](=[O:14])[NH:12][C:11](=[O:15])[NH:10]1)[C:9]1[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=1)[CH2:3][CH2:2]2.C[Si](N([Si](C)(C)C)C(=O)C(F)(F)F)(C)C.[Br:31]Br>C(Cl)(Cl)Cl>[Br:31][CH:3]1[C:4]2[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=2)[C:1]2([C:13](=[O:14])[NH:12][C:11](=[O:15])[NH:10]2)[CH2:2]1

Participants

5

Reactant 3

HCID 24408BromineHCID 65279N,N-Bis(trimethylsilyl)trifluoroacetamideHCID 2338152',3'-Dihydro-2H,5H-spiro[imidazolidine-4,1'-indene]-2,5-dione

Product 1

HCID 135630903'-Bromo-2',3'-dihydro-2H,5H-spiro[imidazolidine-4,1'-indene]-2,5-dioneYield 29%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
25 °C

Procedure

Spiro[imidazolidine-4,1'-indan]2,5-dione, (C.A. reg. no. 6252-98-8) (6.06 g, 30 mmol) was combined with 7.95 ml (30 mmol) bis(trimethylsilyl)trifluoroacetamide and 4.8 g (30 mmol) bromine in 50 ml chloroform and heated to reflux. Decolorization occurred during the 18 hour reaction. The reaction mixture was cooled to 25° C. and after 45 minutes stirring a solid which had crystallized was collected by filtration to give 2.45 g (29%) of crude 3'-bromo-spiro[imidazolidine-4,1'-indan]2,5-dione. The chloroform mother liquors deposited an additional 2.18 g (26% yield), mp 58°-65° C. Two grams (7.1 mmol) of material, mp 58°-65° C., was combined with 25 ml water to give a slurry. Following stirring for 22 hours the resultant solid was collected by filtration and dried to give 0.52 g (33% yield) of the title compound: mp 260°-263° C.

Workup

  1. temperatureheated to reflux
  2. customDecolorization occurred during the 18 hour reaction
  3. customhad crystallized
  4. filtrationwas collected by filtration

Sources & evidence

ORD record
ord-09007e70277143719c4560363768f66f
Source dataset
uspto-grants-1985_12
Patent number
US04556670

Reaction notes

Loading…