Guanidine → N-diaminomethylene-2-methyl-4-ethenyl-5-methylsulfonyl-benzamide

HRID 2895

Reaction equation

HRID 2895 reaction equation
[NH2:1][C:2]([NH2:19])=[N:3][C:4](=[O:18])[C:5]1[CH:10]=[C:9]([S:11]([CH3:14])(=[O:13])=[O:12])[C:8]([C:15]#[CH:16])=[CH:7][C:6]=1[CH3:17].CC1C=C(Br)C(S(C)(=O)=O)=CC=1C(OC)=O.CC1C=C(C#C)C(S(C)(=O)=O)=CC=1C(OC)=O.NC(N)=N.[H][H]>CN(C=O)C.[Pd].C([O-])([O-])=O.[Ca+2]>[NH2:19][C:2]([NH2:1])=[N:3][C:4](=[O:18])[C:5]1[CH:10]=[C:9]([S:11]([CH3:14])(=[O:12])=[O:13])[C:8]([CH:15]=[CH2:16])=[CH:7][C:6]=1[CH3:17]

Participants

8

Reactant 5

HCID 3520GuanidineHCID 10590825Methyl 4-bromo-5-methanesulfonyl-2-methylbenzoateHCID 19688115N-diaminomethylene-2-methyl-4-ethynyl-5-methylsulfonylbenzamideHCID 19688249Methyl 2-methyl-4-ethynyl-5-methylsulfonyl-benzoateHCID 178418361HCID 178418361, compound

Product 1

HCID 19688146N-diaminomethylene-2-methyl-4-ethenyl-5-methylsulfonyl-benzamide

Reagents, catalysts & solvents 2

HCID 12000666Calcium Palladium CarbonateCatalystHCID 6228DimethylformamideSolvent

Procedure

6.0 g of N-diaminomethylene-2-methyl-4-ethynyl-5-methylsulfonylbenzamide, m.p. 223°-226° [obtainable by reaction of methyl 2-methyl-4-bromo-5-methylsulfonyl-benzoate with Li acetylide to give methyl 2-methyl-4-ethynyl-5-methylsulfonyl-benzoate and subsequent reaction with guanidine] are dissolved in 300 ml of DMF and hydrogenated in the presence of 450 mg of Pd-CaCO3 (Lindlar catalyst) for 15 minutes in a stream of hydrogen (p=1 bar). Customary working up gives N-diaminomethylene-2-methyl-4-ethenyl-5-methylsulfonyl-benzamide).

Sources & evidence

ORD record
ord-b9a7eb44685f468d8f6ff10d7448f0ce
Source dataset
uspto-grants-1998_03
Patent number
US05731351

Linked notes

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