O-Phenylenediamine → HCID 178432762, compound

HRID 2423256Notes

Reaction equation

HRID 2423256 reaction equation
[C:1]1([NH2:8])[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[NH2:7].[CH3:9][C:10]1[S:11][C:12]([C:16]([C:18](=[C:37](SC)SC)[C:19]([C:21]2[CH:22]=[C:23]([S:27]([NH:30][C:31](=[NH:36])[C:32]([OH:35])([CH3:34])[CH3:33])(=[O:29])=[O:28])[CH:24]=[CH:25][CH:26]=2)=[O:20])=[O:17])=[C:13]([CH3:15])[N:14]=1>CCO>[NH:7]1[C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][C:1]=2[NH:8][C:37]1=[C:18]([C:16]([C:12]1[S:11][C:10]([CH3:9])=[N:14][C:13]=1[CH3:15])=[O:17])[C:19]([C:21]1[CH:22]=[C:23]([S:27]([NH:30][C:31](=[NH:36])[C:32]([OH:35])([CH3:34])[CH3:33])(=[O:29])=[O:28])[CH:24]=[CH:25][CH:26]=1)=[O:20]

Participants

4

Reactant 2

HCID 7243O-PhenylenediamineHCID 178504084HCID 178504084, compound

Product 1

HCID 178432762HCID 178432762, compoundYield 81.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

1,2-Phenylenediamine (81 mg) was added to an EtOH (20 mL) solution of N-[(3-{2-[(2,4-dimethyl-1,3-thiazol-5-yl)carbonyl]-3,3-bis(methylthio)acryloyl}phenyl)sulfonyl]-2-hydroxy-2-methylpropanimidamide (370 mg), followed by heating under reflux for 13 hours. After cooling, the reaction mixture was concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (chloroform/methanol=50/1), and recrystallized from ethyl acetate/n-hexane to obtain N-({3-[2-(1,3-dihydro-2H-benzimidazol-2-ylidene)-3-(2,4-dimethyl-1,3-thiazol-5-yl)-3-oxopropanoyl]phenyl}sulfonyl)-2-hydroxy-2-methylpropanimidamide (310 mg).

Workup

  1. temperatureby heating
  2. temperatureunder reflux for 13 hours
  3. temperatureAfter cooling
  4. concentrationthe reaction mixture was concentrated under reduced pressure
  5. customThe resulting residue was purified by silica gel column chromatography (chloroform/methanol=50/1)
  6. customrecrystallized from ethyl acetate/n-hexane

Sources & evidence

ORD record
ord-f5c04628f69e4fdfa1e2f7e1e55eccae
Source dataset
uspto-grants-2011_06
Patent number
US07960562B2

Reaction notes

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