Carbon Dioxide → HCID 20345774, compound

HRID 2049106Notes

Reaction equation

HRID 2049106 reaction equation
[C:1]1(=O)O[C:4](=O)[CH:3]=[CH:2]1.CN[C:10]1C=[CH:14][CH:13]=[CH:12][CH:11]=1.[C:16]1([N:22]=[C:23]=[O:24])[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.[CH2:25]1[N:30]2[CH2:31][CH2:32]N([CH2:28][CH2:29]2)C1.C(=O)=[O:34].N1[CH2:42][C:40](=[O:41])[NH:39][C:37]1=O>C1(=O)OCCC1>[C:16]1([N:22]2[CH:42]([CH2:32][C:31]([N:30]([CH3:25])[C:29]3[CH:28]=[CH:4][CH:3]=[CH:2][CH:1]=3)=[O:34])[C:40](=[O:41])[N:39]([C:37]3[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=3)[C:23]2=[O:24])[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

8

Reactant 6

HCID 280Carbon DioxideHCID 7515N-MethylanilineHCID 7672Phenyl isocyanateHCID 7923Maleic AnhydrideHCID 9237DabcoHCID 10006Hydantoin

Product 1

HCID 20345774HCID 20345774, compound

Reagents, catalysts & solvents 1

HCID 7302Gamma-ButyrolactoneSolvent

Conditions

Temperature
150 °C

Procedure

103 g of the amido acid of maleic acid anhydride and N-methyl aniline are dissolved in 200 g of butyrolactone. 119 g of phenyl isocyanate are then added dropwise at 20° to 25° C. 0.2 g of triethylene diamine are then added and the mixture is stirred for 2 hours at 50° C., for 2 hours at 100° C. and for 4 hours at 150° C. The condensation and ring-forming reaction are accompanied by the elimination of carbon dioxide. On completion of the reaction, 112 g of the hydantoin melting at 191° C. crystallise out on cooling. Another 17 g are obtained from the filtrate by precipitation with water and recrystallisation from ethanol/dioxane (3:1). After another recrystallisation from ethanol/dioxane, 1,3-diphenyl-5-(N-methyl-N-phenylaminocarbonylmethyl)-hydantoin is obtained in the form of almost colourless crystals melting at 195° to 196° C. In the IR-spectrum, the compound shows the bands typical of hydantoins at 1720 and 1780 cm-1 and a band corresponding to amide at 1645 cm-1.

Workup

  1. customThe condensation
  2. customring-forming
  3. customreaction
  4. customcrystallise out
  5. temperatureon cooling
  6. customAnother 17 g are obtained from the filtrate by precipitation with water and recrystallisation from ethanol/dioxane (3:1)
  7. customAfter another recrystallisation from ethanol/dioxane

Sources & evidence

ORD record
ord-def95b26c9ad4edbb21beaf72cc1305a
Source dataset
uspto-grants-1980_04
Patent number
US04196274

Reaction notes

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