Guanidine → HCID 9906200, compound

HRID 1289215Notes

Reaction equation

HRID 1289215 reaction equation
[CH3:1][S:2]([C:5]1[CH:6]=[C:7]([CH:12]=[CH:13][C:14]=1[C:15]([F:18])([F:17])[F:16])[C:8](OC)=[O:9])(=[O:4])=[O:3].CS(C1C=C(C=CC=1Br)C(OC)=O)(=O)=O.FC(F)(F)C([O-])=O.[K+].[NH2:42][C:43]([NH2:45])=[NH:44]>[I-].C[N+](C)(C)C.C1(C)C=CC=CC=1.CO.[Cu]I>[NH2:44][C:43]([NH2:45])=[N:42][C:8](=[O:9])[C:7]1[CH:12]=[CH:13][C:14]([C:15]([F:18])([F:17])[F:16])=[C:5]([S:2]([CH3:1])(=[O:4])=[O:3])[CH:6]=1

Participants

9

Reactant 4

HCID 3520GuanidineHCID 10708002HCID 10708002, compoundHCID 11109119methyl 3-methylsulfonyl-4-bromobenzoateHCID 23662811Potassium trifluoroacetate

Product 1

HCID 9906200HCID 9906200, compound

Reagents, catalysts & solvents 4

HCID 638175-58-1CatalystHCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 887MethanolSolventHCID 1140TolueneSolvent

Procedure

1.1 g of methyl 3-methylsulfonyl-4-trifluoromethylbenzoate [m.p. 146°-147°; obtainable by reaction of methyl 3-methylsulfonyl-4-bromobenzoate with potassium trifluoroacetate in the presence of CuI and tetramethylammonium iodide in toluene] are added to a solution of 928 mg of guanidine in 15 ml of methanol. The mixture is stirred for 45 minutes at 50° and, after removal of the solvent and customary working up, N-diaminomethylene3-methylsulfonyl-4-trifluoromethylbenzamide, m.p. 233°-234°, is obtained.

Workup

  1. customafter removal of the solvent

Sources & evidence

ORD record
ord-1e03e6046513426fbf3827f81c803807
Source dataset
uspto-grants-1998_05
Patent number
US05747539

Reaction notes

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