Imidazole → HCID 86752580, compound

HRID 1291036Notes

Reaction equation

HRID 1291036 reaction equation
[NH2:1][C:2]([NH2:4])=[NH:3].CC1C=C([N:16]2[CH:20]=[CH:19][N:18]=[CH:17]2)C(S(C)(=O)=O)=CC=1C(OC)=O.[CH3:25][CH:26]1[C:34](=[S:35](=[O:37])=[O:36])[C:33](Cl)=[C:32]([CH3:39])[CH:31]=[C:27]1[C:28]([OH:30])=O.N1C=CN=C1.[H-].[Na+]>CN1CCCC1=O.CO.O>[NH2:3][C:2]([NH2:4])=[N:1][C:28](=[O:30])[C:27]1[CH:26]([CH3:25])[C:34](=[S:35](=[O:37])=[O:36])[C:33]([N:16]2[CH:20]=[CH:19][N:18]=[CH:17]2)=[C:32]([CH3:39])[CH:31]=1

Participants

9

Reactant 5

HCID 795ImidazoleHCID 3520GuanidineHCID 24758Sodium hydrideHCID 10565715HCID 10565715, compoundHCID 86752581HCID 86752581, compound

Product 1

HCID 86752580HCID 86752580, compound

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

A solution of 2.54 g of guanidine and 2.41 g of methyl 2-methyl-4-(1-imidazolyl)-5-methylsulfonylbenzoate [obtainable by reacting 2-methyl-4-chloro-5-methyl-sulfonylbenzoic acid with imidazole in the presence of NaH in N-methylpyrrolidone followed by esterification] in 20 ml of methanol is stirred at 500 for 3 hours. Water is then added to the reaction mixture, and the crude product which precipitates out is filtered off with suction and recrystallized from methanol. N-Diaminomethylene-2-methyl-4-(1-imidazolyl)-5-methyl-sulfonylbenzamide, m.p. 236°, is obtained.

Workup

  1. customthe crude product which precipitates out
  2. filtrationis filtered off with suction
  3. customrecrystallized from methanol

Sources & evidence

ORD record
ord-e16e06a742454f8388cc1b8c4c8f0134
Source dataset
uspto-grants-1998_05
Patent number
US05753680

Reaction notes

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