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

HRID 260210Notes

Reaction equation

HRID 260210 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][CH2:23][CH2:24][C:25](Cl)=[O:26]>>[Br:22][CH2:23][CH2:24][C:25]([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:26]

Participants

3

Reactant 2

HCID 84944Propanoyl chloride, 3-bromo-HCID 1613663-(Hydroxymethyl)phenytoin

Product 1

HCID 147506993-(3'-Bromopropionyl)oxymethyl-5,5-diphenyl-2,4-imidazolidinedioneYield 65%

Procedure

5,5-Diphenyl-3-hydroxymethyl-2,4-imidazolidinedione (5 g, 0.018 tool) was reacted according to the procedure of Example 142 with 3-bromopropionyl chloride (6.8 g, 0.04 mol, 4 ml), using a bath temperature of 100° C. A white crystalline product was obtained in 65% yield (4.9 g), m.p. 133°-134° C. Anal. calc. for C19H17N2O4Br: C, 54.69; H, 4.11; N, 6.72; Br, 19.15. Found: C, 54.79; H, 4.12; N, 6.69; Br, 19.25. The product has the formula: ##STR1523##

Workup

  1. customtemperature of 100° C
  2. customA white crystalline product was obtained in 65% yield (4.9 g), m.p. 133°-134° C

Sources & evidence

ORD record
ord-d285aa8174c24594a1d05d705524fa37
Source dataset
uspto-grants-1996_06
Patent number
US05525727

Reaction notes

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