Formaldehyde → 9-(1H-Imidazol-1-yl)-4-[(4-methylphenyl)sulfonyl]-3,4,5,6-tetrahydro-2H-1,7,4-benzodioxazonine

HRID 1089547Notes

Reaction equation

HRID 1089547 reaction equation
[NH2:1][C:2]1[CH:24]=[CH:23][C:5]2[O:6][CH2:7][CH2:8][N:9]([S:13]([C:16]3[CH:21]=[CH:20][C:19]([CH3:22])=[CH:18][CH:17]=3)(=[O:15])=[O:14])[CH2:10][CH2:11][O:12][C:4]=2[CH:3]=1.[OH-].[NH4+:26].[CH:27]([CH:29]=O)=O.[CH2:31]=O>>[N:1]1([C:2]2[CH:24]=[CH:23][C:5]3[O:6][CH2:7][CH2:8][N:9]([S:13]([C:16]4[CH:21]=[CH:20][C:19]([CH3:22])=[CH:18][CH:17]=4)(=[O:15])=[O:14])[CH2:10][CH2:11][O:12][C:4]=3[CH:3]=2)[CH:29]=[CH:27][N:26]=[CH:31]1

Participants

5

Reactant 4

HCID 712FormaldehydeHCID 7860GlyoxalHCID 14923Ammonium HydroxideHCID 148563569-Amino-4-[(4-methylphenyl)sulfonyl]-3,4,5,6-tetrahydro-2H-1,7,4-benzodioxazonine

Product 1

HCID 148563589-(1H-Imidazol-1-yl)-4-[(4-methylphenyl)sulfonyl]-3,4,5,6-tetrahydro-2H-1,7,4-benzodioxazonine

Procedure

To reagent alcohol at 60° C. simultaneously add a solution of 9-amino-4-[(4-methylphenyl)sulfonyl]-3,4,5,6-tetrahydro-2H-1,7,4-benzodioxazonine and ammonium hydroxide diluted with alcohol and a solution of aqueous glyoxal and aqueous formaldehyde diluted to an equal volume with alcohol as the above solution. Monitor the progress of the reaction by thin-layer chromatography. Upon completion partition the reaction between ethyl acetate and aqueous NaHCO3. Separate and dry the organic layer (Na2SO4). Remove the solvent in vacuo to obtain the title compound.

Workup

  1. customMonitor the progress of the reaction by thin-layer chromatography
  2. customUpon completion partition
  3. customthe reaction between ethyl acetate and aqueous NaHCO3
  4. customSeparate
  5. dry with materialdry the organic layer (Na2SO4)
  6. customRemove the solvent in vacuo

Sources & evidence

ORD record
ord-bd327465f0044438a5b13a47d125538d
Source dataset
uspto-grants-1990_10
Patent number
US04966967

Reaction notes

Loading…