Formaldehyde → 1-Methyl-3-(2-methoxyphenylaminomethyl)hydantoin

HRID 973110Notes

Reaction equation

HRID 973110 reaction equation
[CH3:1][O:2][C:3]1[C:4]([NH2:9])=[CH:5][CH:6]=[CH:7][CH:8]=1.[CH2:10]=O.[CH3:12][N:13]1[CH2:19][C:17](=[O:18])[NH:16][C:14]1=[O:15]>C(O)C.CCOCC>[CH3:12][N:13]1[CH2:19][C:17](=[O:18])[N:16]([CH2:10][NH:9][C:4]2[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=2[O:2][CH3:1])[C:14]1=[O:15]

Participants

6

Reactant 3

HCID 712FormaldehydeHCID 70002-MethoxyanilineHCID 692171-Methylhydantoin

Product 1

HCID 203160711-Methyl-3-(2-methoxyphenylaminomethyl)hydantoinYield 48.2%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 3283Diethyl EtherSolvent

Procedure

A mixture of 12.3 g of o-anisidine, 3.3 g of paraformaldehyde, and 11.4 g of 1-methylhydantoin in 100 ml of absolute ethanol was refluxed for 8 hrs under nitrogen atmosphere. At the end of this time, the solution was cooled on a dry ice-acetone bath and the solvent was decanted to leave a viscous oil. The oil was dissolved in 800 ml of ether and the etheral solution was allowed to evaporate slowly at room temperature. The resulting precipitate was filtered to give 12 g of 1-methyl-3-(2-methoxyphenylaminomethyl)hydantoin, mp 93°-96.5° C, identified by IR and NMR.

Workup

  1. temperaturewas refluxed for 8 hrs under nitrogen atmosphere
  2. temperatureAt the end of this time, the solution was cooled on a dry ice-acetone bath
  3. customthe solvent was decanted
  4. customto leave a viscous oil
  5. customto evaporate slowly at room temperature
  6. filtrationThe resulting precipitate was filtered

Sources & evidence

ORD record
ord-1077a8067c83410baa82691a80d0593a
Source dataset
uspto-grants-1977_10
Patent number
US04055410

Reaction notes

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