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

HRID 1085194Notes

Reaction equation

HRID 1085194 reaction equation
[C:1]1([C:7]2([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[NH:11][C:10](=[O:12])[N:9]([CH2:13][OH:14])[C:8]2=[O:15])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Br:22][CH:23]([CH3:27])[C:24](Cl)=[O:25]>C(OCC)C>[Br:22][CH:23]([CH3:27])[C:24]([O:14][CH2:13][N:9]1[C:8](=[O:15])[C:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)([C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)[NH:11][C:10]1=[O:12])=[O:25]

Participants

4

Reactant 2

HCID 979802-Bromopropanoyl chlorideHCID 1613663-(Hydroxymethyl)phenytoin

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-imidazolidinedione (2 g, 0.0071 mol) 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: ##STR1545##

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-09be3ba6eac2484f9cdf89cd291bf896
Source dataset
uspto-grants-1991_04
Patent number
US05008257

Reaction notes

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