Sodium Hydroxide → 2-[(6-Benzenesulfonyl-naphthalen-1-ylmethyl)-amino]-3,5-dihydro-imidazol-4-one

HRID 1715063Notes

Reaction equation

HRID 1715063 reaction equation
[C:1]1([S:7]([C:10]2[CH:11]=[C:12]3[C:17](=[CH:18][CH:19]=2)[C:16]([CH2:20][NH2:21])=[CH:15][CH:14]=[CH:13]3)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CS[C:24]1[NH:28][C:27](=[O:29])[CH2:26][N:25]=1.[OH-].[Na+]>C(O)C>[C:1]1([S:7]([C:10]2[CH:11]=[C:12]3[C:17](=[CH:18][CH:19]=2)[C:16]([CH2:20][NH:21][C:24]2[NH:28][C:27](=[O:29])[CH2:26][N:25]=2)=[CH:15][CH:14]=[CH:13]3)(=[O:9])=[O:8])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 137567813,5-dihydro-2-(methylthio)-4H-Imidazol-4-oneHCID 59028770C-(6-Benzenesulfonyl-naphthalen-1-yl)-methylamine

Product 1

HCID 590287842-[(6-Benzenesulfonyl-naphthalen-1-ylmethyl)-amino]-3,5-dihydro-imidazol-4-one

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of C-(6-Benzenesulfonyl-naphthalen-1-yl)-methylamine, 2-methylsulfanyl-3,5-dihydro-imidazol-4-one (prepared by the method reported by Chen et al., WO9736859) and sodium hydroxide in ethanol is heated to reflux, then concentrated under reduced pressure, diluted with ethyl acetate, and washed with aqueous sodium carbonate. The organic phase is dried (magnesium sulfate) and concentrated under reduced pressure to give 2-[(6-benzenesulfonyl-naphthalen-1-ylmethyl)-amino]-3,5-dihydro-imidazol-4-one.

Workup

  1. customprepared by the method
  2. temperatureis heated
  3. temperatureto reflux
  4. concentrationconcentrated under reduced pressure
  5. additiondiluted with ethyl acetate
  6. washwashed with aqueous sodium carbonate
  7. dry with materialThe organic phase is dried (magnesium sulfate)
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-e448adc7ba1f4c95b1b6b1cf227f6c9d
Source dataset
uspto-grants-2010_09
Patent number
US07799797B2

Reaction notes

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