Diazald → HCID 53380167, compound

HRID 2388600Notes

Reaction equation

HRID 2388600 reaction equation
[OH-].[K+].[CH3:3]C1C=CC(S(N(N=O)C)(=O)=O)=CC=1.C(O)CO.CCOCC.[NH:26]1[C:30]2[CH:31]=[CH:32][C:33]([N:35]3[CH:39]([C:40]4[CH:45]=[CH:44][CH:43]=[C:42]([Cl:46])[C:41]=4[Cl:47])[C:38]([CH3:48])=[C:37]([OH:49])[C:36]3=[O:50])=[CH:34][C:29]=2[N:28]=[CH:27]1>CO>[NH:28]1[C:29]2[CH:34]=[C:33]([N:35]3[CH:39]([C:40]4[CH:45]=[CH:44][CH:43]=[C:42]([Cl:46])[C:41]=4[Cl:47])[C:38]([CH3:48])=[C:37]([O:49][CH3:3])[C:36]3=[O:50])[CH:32]=[CH:31][C:30]=2[N:26]=[CH:27]1

Participants

6

Reactant 4

HCID 6628DiazaldHCID 14797Potassium HydroxideHCID 21225595HCID 21225595, compoundHCID 178431715HCID 178431715, compound

Product 1

HCID 53380167HCID 53380167, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The compound was synthesized starting from KOH (9.0 g,160.71 mmol in water), diazald (24 g, 112.02 mmol), ethylene glycol/Et2O (2/1 v/v, 140 mL), 1-(1H-benzo[d]imidazol-5-yl)-5-(2,3-dichlorophenyl)-3-hydroxy-4-methyl-1H-pyrrol-2(5H)-one (3 g, 8.04 mmol, 1 eq) and MeOH (50 mL); yield: 1.2 g (38.46%); MS m/z: 388.1 [M+H]+; 1H-NMR: (400 MHz, DMSO-D6) δ: 12.44 (s, 1H), 8.16 (d, 1H), 7.64 (d, 1H), 7.54-7.40 (m, 2H), 7.32-7.18 (m, 3H), 7.08 (t, 1H), 6.31 (s, 1H), 3.96 (s, 3H), 1.73 (s, 3H); HPLC (METHOD [A]): rt 13.75 min (99.4%)

Workup

  1. customThe compound was synthesized
  2. customrt 13.75 min (99.4%)

Sources & evidence

ORD record
ord-38d996faa72d448aa604788e5b0ee52d
Source dataset
uspto-grants-2012_09
Patent number
US08269019B2

Reaction notes

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