Ammonia → 4-(2,4-Dichloro-5-sulfamoylphenyl)-3-methyl-2-methylimino-1,3-thiazolidine-4-ol

HRID 460834Notes

Reaction equation

HRID 460834 reaction equation
Br.[Cl:2][C:3]1[CH:8]=[C:7]([Cl:9])[C:6]([S:10](Cl)(=[O:12])=[O:11])=[CH:5][C:4]=1[C:14]1([OH:22])[CH2:18][S:17][C:16](=[N:19][CH3:20])[N:15]1[CH3:21].[NH3:23]>CO>[Cl:2][C:3]1[CH:8]=[C:7]([Cl:9])[C:6]([S:10](=[O:12])(=[O:11])[NH2:23])=[CH:5][C:4]=1[C:14]1([OH:22])[CH2:18][S:17][C:16](=[N:19][CH3:20])[N:15]1[CH3:21]

Participants

4

Reactant 2

HCID 222AmmoniaHCID 213947574-(2,4-Dichlor-5-chlorosulfonylphenyl)-3-methyl-2-methylimino-1,3-thiazolidine-4-ol-hydrobromide

Product 1

HCID 213947694-(2,4-Dichloro-5-sulfamoylphenyl)-3-methyl-2-methylimino-1,3-thiazolidine-4-ol

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

4.4 g of 4-(2,4-dichlor-5-chlorosulfonylphenyl)-3-methyl-2-methylimino-1,3-thiazolidine-4-ol-hydrobromide were introduced, while stirring, into a solution of 10 g of gaseous ammonia in 70 ml of methanol. After having allowed the whole to stand overnight at room temperature, the solution was concentrated to about 30 ml of its volume under reduced pressure and the 4-(2,4-dichloro-5-sulfamoylphenyl)-3-methyl-2-methylimino-1,3-thiazolidine-4-ol was precipitated with 100 ml of water. M.p. 186°-189° C (decomposition ).

Workup

  1. concentrationthe solution was concentrated to about 30 ml of its volume under reduced pressure
  2. customthe 4-(2,4-dichloro-5-sulfamoylphenyl)-3-methyl-2-methylimino-1,3-thiazolidine-4-ol was precipitated with 100 ml of water

Sources & evidence

ORD record
ord-616116e7316d4819bb38c8d4348c99b8
Source dataset
uspto-grants-1977_12
Patent number
US04061647

Reaction notes

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