2-Bromopropanoyl chloride → 3-(2'-Bromopropionyl)oxymethyl-5,5-diphenyl-2,4-imidazolidinedione

HRID 260211Notes

Reaction equation

HRID 260211 reaction equation
N1CC(=O)NC1=O.[C:8]1([C:14]2([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[NH:18][C:17](=[O:19])[N:16]([CH2:20][OH:21])[C:15]2=[O:22])[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[Br:29][CH:30]([CH3:34])[C:31](Cl)=[O:32]>C(OCC)C>[Br:29][CH:30]([CH3:34])[C:31]([O:21][CH2:20][N:16]1[C:15](=[O:22])[C:14]([C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=2)([C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=2)[NH:18][C:17]1=[O:19])=[O:32]

Participants

4

Reactant 2

HCID 979802-Bromopropanoyl chlorideHCID 67747558HCID 67747558, compound

Product 1

HCID 147507003-(2'-Bromopropionyl)oxymethyl-5,5-diphenyl-2,4-imidazolidinedione

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

5,5-Diphenyl-3-hydroxymethyl-2,4-imidazolidine-dione imidazolidinedione (2 g, 0.0071 tool) was dissolved in 2-bromopropionyl chloride (8.5 g, 5 ml, 0.05 mol) by heating for 30 minutes on a 100°-110° C. oil bath. The reaction mixture was cooled, 20 ml of ethyl ether were added, and the resultant solution was extracted with aqueous potassium carbonate, dried and then crystallized. The product was obtained as a solid white substance (1 g, 34% ), m.p. 112°-115° C. Anal. calc. for C19H17N2O4Br: C, 54.69; H, 4.11; N, 6.72; Br, 19.15. Found: C, 54.77; H, 4.15; N, 6.69; Br, 19.25. The product has the formula: ##STR1524##

Workup

  1. temperatureby heating for 30 minutes on a 100°-110° C. oil bath
  2. temperatureThe reaction mixture was cooled
  3. extractionthe resultant solution was extracted with aqueous potassium carbonate
  4. customdried
  5. customcrystallized
  6. customThe product was obtained as a solid white substance (1 g, 34% ), m.p. 112°-115° C

Sources & evidence

ORD record
ord-3398696e7fff45f99d56a131dadee296
Source dataset
uspto-grants-1996_06
Patent number
US05525727

Reaction notes

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