Guanidine → N-diaminomethylene-2-methyl-4-bromo-5-methylsulphonylbenzamide

HRID 1457949Notes

Reaction equation

HRID 1457949 reaction equation
[CH3:1][C:2]1[CH:11]=[C:10]([Br:12])[C:9]([S:13]([CH3:16])(=[O:15])=[O:14])=[CH:8][C:3]=1[C:4](OC)=[O:5].[NH2:17][C:18]([NH2:20])=[NH:19]>CO>[NH2:19][C:18]([NH2:20])=[N:17][C:4](=[O:5])[C:3]1[CH:8]=[C:9]([S:13]([CH3:16])(=[O:15])=[O:14])[C:10]([Br:12])=[CH:11][C:2]=1[CH3:1]

Participants

4

Reactant 2

HCID 3520GuanidineHCID 10590825Methyl 4-bromo-5-methanesulfonyl-2-methylbenzoate

Product 1

HCID 10830518N-diaminomethylene-2-methyl-4-bromo-5-methylsulphonylbenzamide

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 1.8 g of methyl 2-methyl-4-bromo-5-methylsulphonylbenzoate [obtainable in accordance with Ex. 1] and 1.5 g of guanidine in 50 ml of methanol is boiled for five hours, and the solvent is subsequently 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-bromo-5-methylsulphonylbenzamide is obtained, m.p. 207°-208°.

Workup

  1. customthe solvent is subsequently 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-f2e65e16a3b9461baa6d04fc1bf7ecd8
Source dataset
uspto-grants-1998_12
Patent number
US05849796

Reaction notes

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