Guanidine → HCID 9798264, compound

HRID 2393640Notes

Reaction equation

HRID 2393640 reaction equation
[CH3:1][C:2]1[CH:11]=[C:10]([C:12]2[CH:17]=[CH:16][C:15]([CH3:18])=[CH:14][CH:13]=2)[C:9]([S:19]([CH3:22])(=[O:21])=[O:20])=[CH:8][C:3]=1[C:4](OC)=[O:5].[NH2:23][C:24]([NH2:26])=[NH:25]>CO>[NH2:25][C:24]([NH2:26])=[N:23][C:4](=[O:5])[C:3]1[CH:8]=[C:9]([S:19]([CH3:22])(=[O:21])=[O:20])[C:10]([C:12]2[CH:17]=[CH:16][C:15]([CH3:18])=[CH:14][CH:13]=2)=[CH:11][C:2]=1[CH3:1]

Participants

4

Reactant 2

HCID 3520GuanidineHCID 10519596HCID 10519596, compound

Product 1

HCID 9798264HCID 9798264, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 1.8 g of methyl 2-methyl-4-(4-methylphenyl) -5-methylsulphonylbenzoate [obtainable by reacting methyl 3-methylsulphonyl-4-bromo-6-methylbenzoate with tolylboronic acid] 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 crop of crystals which remains is filtered off with suction and treated with dilute sodium hydroxide solution. The solid residue is filtered off and recrystallized from ethanol, and N-diaminomethylene-2-methyl-4-(4-methylphenyl)-5-methylsulphonylbenzamide is obtained, m.p. 222°-224°.

Workup

  1. customthe solvent is then removed
  2. additionThe residue is treated with water
  3. filtrationthe crop of crystals which remains is filtered off with suction
  4. additiontreated with dilute sodium hydroxide solution
  5. filtrationThe solid residue is filtered off
  6. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-32c00a517e4d454ba62d7ef2eef52960
Source dataset
uspto-grants-1998_09
Patent number
US05807896

Reaction notes

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