Dimethylamine → Metibride

HRID 67779Notes

Reaction equation

HRID 67779 reaction equation
Br.[Cl:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[N:10]([CH3:21])[C:11](=[N:14][C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[S:12][CH:13]=2)=[CH:5][C:4]=1[S:22](Cl)(=[O:24])=[O:23].[CH3:26][NH:27][CH3:28].CO>C(O)C>[Cl:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[N:10]([CH3:21])[C:11](=[N:14][C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[S:12][CH:13]=2)=[CH:5][C:4]=1[S:22](=[O:24])(=[O:23])[N:27]([CH3:28])[CH3:26]

Participants

5

Reactant 3

HCID 674DimethylamineHCID 887MethanolHCID 205273464-(4-Chloro-3-chlorosulfonylphenyl)-3-methyl-2-phenylimino-4-thiazoline hydrobromide

Product 1

HCID 3047726Metibride

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

4.8 g (0.01 mole) of 4-(4-chloro-3-chlorosulfonylphenyl)-3-methyl-2-phenylimino-4-thiazoline hydrobromide are added in portions to a mixture of 5 ml (about 0.05 mole) of 40% strength aqueous dimethylamine solution and 50 ml of methanol (or ethanol), with external cooling and stirring, at a rate such that the temperature as far as possible does not rise above 35° C. The reaction mixture is stirred for 14 hours at room temperature, the solvent is distilled off under a waterpump vacuum and the residue is crystallized under 50 ml of water, stirring with a magnetic stirrer. Colorless crystals; melting point 178°-181° C.

Workup

  1. temperaturewith external cooling
  2. customas possible does not rise above 35° C
  3. stirringThe reaction mixture is stirred for 14 hours at room temperature
  4. distillationthe solvent is distilled off under a waterpump vacuum
  5. customthe residue is crystallized under 50 ml of water
  6. stirringstirring with a magnetic stirrer

Sources & evidence

ORD record
ord-62dda4ab69944a608947378d9c4e1016
Source dataset
uspto-grants-1982_08
Patent number
US04346088

Reaction notes

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