Diisopropyl Ether → 4-(4-Chloro-3-dimethylsulfamoylphenyl)-3-methyl-2-(2,4-dimethylphenyl-imino)-4-thiazoline hydrobromide

HRID 67777Notes

Reaction equation

HRID 67777 reaction equation
[Br:1][CH2:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([Cl:11])=[C:7]([S:12](=[O:17])(=[O:16])[N:13]([CH3:15])[CH3:14])[CH:6]=1)=O.[CH3:18][NH:19][C:20](=[S:30])[NH:21][C:22]1[CH:27]=[CH:26][C:25]([CH3:28])=[CH:24][C:23]=1[CH3:29].C(OCC)(=O)C.C(OC(C)C)(C)C>C(O)(=O)C>[BrH:1].[Cl:11][C:8]1[CH:9]=[CH:10][C:5]([C:3]2[N:19]([CH3:18])[C:20](=[N:21][C:22]3[CH:27]=[CH:26][C:25]([CH3:28])=[CH:24][C:23]=3[CH3:29])[S:30][CH:2]=2)=[CH:6][C:7]=1[S:12](=[O:17])(=[O:16])[N:13]([CH3:15])[CH3:14]

Participants

6

Reactant 4

HCID 7914Diisopropyl EtherHCID 8857Ethyl AcetateHCID 30342141-(2,4-Dimethylphenyl)-3-methylthioureaHCID 204768462-Bromo-4'-chloro-3'-dimethylsulfamoylacetophenone

Product 1

HCID 205272334-(4-Chloro-3-dimethylsulfamoylphenyl)-3-methyl-2-(2,4-dimethylphenyl-imino)-4-thiazoline hydrobromide

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

3.41 g (0.01 mole) of 2-bromo-4'-chloro-3'-dimethylsulfamoyl-acetophenone are added to a solution of 1.83 g (0.01 mole) of 3-methyl-1-(2,4-dimethylphenyl)thiourea in 60 ml of glacial acetic acid and the mixture is stirred at room temperature for 20 minutes. It is then boiled for 20 minutes under a reflux condenser and allowed to cool, 60 ml of ethyl acetate or diisopropyl ether are added to the reaction mixture and the crystals are filtered off. Melting point 260°-264° C. (with decomposition).

Workup

  1. waitIt is then boiled for 20 minutes under a reflux condenser
  2. temperatureto cool
  3. filtrationthe crystals are filtered off

Sources & evidence

ORD record
ord-ca1870352c5b4abfafa75b730fe52dfd
Source dataset
uspto-grants-1982_08
Patent number
US04346088

Reaction notes

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