Guanidine → N-diaminomethylene-3-methylsulfonyl-4-(6-methyl-3-pyridyloxy)benzamide

HRID 376867Notes

Reaction equation

HRID 376867 reaction equation
[NH2:1][C:2]([NH2:4])=[NH:3].[CH3:5][S:6]([C:9]1[CH:10]=[C:11]([CH:16]=[CH:17][C:18]=1[O:19][C:20]1[CH:21]=[N:22][C:23]([CH3:26])=[CH:24][CH:25]=1)[C:12](OC)=[O:13])(=[O:8])=[O:7].CS(C1C=C(C=CC=1Cl)C(O)=O)(=O)=O.CC1N=CC(O[Si](C)(C)C)=CC=1.CI.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[NH2:3][C:2]([NH2:4])=[N:1][C:12](=[O:13])[C:11]1[CH:16]=[CH:17][C:18]([O:19][C:20]2[CH:21]=[N:22][C:23]([CH3:26])=[CH:24][CH:25]=2)=[C:9]([S:6]([CH3:5])(=[O:7])=[O:8])[CH:10]=1

Participants

7

Reactant 5

HCID 3520GuanidineHCID 1826704-Chloro-3-methanesulfonylbenzoic acidHCID 5972723-Trimethylsilyloxy-6-methylpyridineHCID 19360282Methyl 3-methylsulfonyl-4-(6-methyl-3-pyridyloxy)benzoateHCID 86747754Methyl iodide potassium carbonate

Product 1

HCID 19360327N-diaminomethylene-3-methylsulfonyl-4-(6-methyl-3-pyridyloxy)benzamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In analogy with Example 2, reacting guanidine with methyl 3-methylsulfonyl-4-(6-methyl-3-pyridyloxy)benzoate [obtainable by reacting 3-methylsulfonyl-4-chlorobenzoic acid with 6-methyl-3-trimethylsilyloxypyridine and subsequently esterifying the product with methyl iodide/K2CO3 in DMF] gives N-diaminomethylene-3-methylsulfonyl-4-(6-methyl-3-pyridyloxy)benzamide, m.p. 197-199°.

Sources & evidence

ORD record
ord-8a308bace9b54b38b6f6379e4235840f
Source dataset
uspto-grants-2000_02
Patent number
US06022883

Reaction notes

Loading…