Guanidine → N-diaminomethylene-2-methyl-4-isopropyl-5-methylsulfonylbenzamide

HRID 357300Notes

Reaction equation

HRID 357300 reaction equation
[CH3:1][C:2]1[CH:11]=[C:10]([CH:12]([CH3:14])[CH3:13])[C:9]([S:15]([CH3:18])(=[O:17])=[O:16])=[CH:8][C:3]=1[C:4](OC)=[O:5].CC1C=C(Br)C(S(C)(=O)=O)=CC=1C(OC)=O.[Cl-].C([Zn+])(C)C.[NH2:40][C:41]([NH2:43])=[NH:42]>CO.[Cu]I>[NH2:42][C:41]([NH2:43])=[N:40][C:4](=[O:5])[C:3]1[CH:8]=[C:9]([S:15]([CH3:18])(=[O:17])=[O:16])[C:10]([CH:12]([CH3:14])[CH3:13])=[CH:11][C:2]=1[CH3:1]

Participants

7

Reactant 4

HCID 3520GuanidineHCID 10590825Methyl 4-bromo-5-methanesulfonyl-2-methylbenzoateHCID 15342084Methyl 2-methyl-4-isopropyl-5-methylsulfonylbenzoateHCID 178461829HCID 178461829, compound

Product 1

HCID 9904301N-diaminomethylene-2-methyl-4-isopropyl-5-methylsulfonylbenzamide

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 887MethanolSolvent

Procedure

A solution of 1.4 g of methyl 2-methyl-4-isopropyl-5-methylsulfonylbenzoate [obtainable by reacting methyl 2-methyl-4-bromo-5-methylsulfonylbenzoate with isopropylzinc chloride in the presence of Pd(II) 1,1'-bis(diphenylphosphine)ferrocene chloride and CuI] and 1.5 g of guanidine in 50 ml of methanol is boiled for five hours and the solvent is then removed. The residue is treated with water and the remaining crystalline crop is filtered off with suction and treated with dil. sodium hydroxide solution. The solid residue is filtered off and recrystallized from ethanol, and N-diaminomethylene-2-methyl-4-isopropyl-5-methylsulfonylbenzamide is obtained, m.p. 220°-223°.

Workup

  1. customthe solvent is then removed
  2. additionThe residue is treated with water
  3. filtrationthe remaining crystalline crop is filtered off with suction
  4. additiontreated with dil. sodium hydroxide solution
  5. filtrationThe solid residue is filtered off
  6. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-05810ac3e3f44006b61c7274743d183e
Source dataset
uspto-grants-1998_11
Patent number
US05840761

Reaction notes

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