1,3-Dipropyl-2-thiourea → 4-(4-Chloro-3-dimethylsulfamoylphenyl)-3-propyl-2-propylimino-1,3-thiazolidine-4-ol-hydrochloride

HRID 1703926Notes

Reaction equation

HRID 1703926 reaction equation
BrCC(C1C=CC([Cl:11])=C(S(=O)(=O)N(C)C)C=1)=O.C(NC(NCCC)=S)CC.Br.[Cl:29][C:30]1[CH:35]=[CH:34][C:33]([C:36]2([OH:48])[CH2:40][S:39][C:38](=[N:41][CH2:42][CH2:43][CH3:44])[N:37]2[CH2:45][CH2:46][CH3:47])=[CH:32][C:31]=1[S:49](=[O:54])(=[O:53])[N:50]([CH3:52])[CH3:51]>C(OCC)C>[ClH:11].[Cl:29][C:30]1[CH:35]=[CH:34][C:33]([C:36]2([OH:48])[CH2:40][S:39][C:38](=[N:41][CH2:42][CH2:43][CH3:44])[N:37]2[CH2:45][CH2:46][CH3:47])=[CH:32][C:31]=1[S:49](=[O:54])(=[O:53])[N:50]([CH3:52])[CH3:51]

Participants

5

Reactant 3

HCID 28012141,3-Dipropyl-2-thioureaHCID 204768462-Bromo-4'-chloro-3'-dimethylsulfamoylacetophenoneHCID 227606734-(4-Chloro-3-dimethylsulfamoylphenyl)-3-propyl-2-propylimino-1,3-thiazolidine-4-ol-hydrobromide

Product 1

HCID 227606754-(4-Chloro-3-dimethylsulfamoylphenyl)-3-propyl-2-propylimino-1,3-thiazolidine-4-ol-hydrochloride

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

6.8 g of 2-bromo-4'-chloro-3'-dimethylsulfamoylacetophenone were reacted according to Example 23 with 3.3 g of 1,3-dipropylthiourea. After adding 200 ml of diethyl ether, 4-(4-chloro-3-dimethylsulfamoylphenyl)-3-propyl-2-propylimino-1,3-thiazolidine-4-ol-hydrobromide was separated as an oil. The solvent was decanted, the product was dissolved in 30 ml of water and extracted with 100 ml of ethyl acetate. After drying over sodium sulfate, the solvent was distilled off under reduced pressure, the amorphous residue was dissolved in 30 ml of ethanol and acidified with ethanolic hydrochloric acid. The solvent was distilled off, the residue was dissolved in 40 ml of water and the end product was obtained by lyophilization. Colorless amorphous solid body, decomposition beginning at 128° C., γ C=N 1615 cm-1.

Workup

  1. customwas separated as an oil
  2. customThe solvent was decanted
  3. dissolutionthe product was dissolved in 30 ml of water
  4. extractionextracted with 100 ml of ethyl acetate
  5. dry with materialAfter drying over sodium sulfate
  6. distillationthe solvent was distilled off under reduced pressure
  7. dissolutionthe amorphous residue was dissolved in 30 ml of ethanol
  8. distillationThe solvent was distilled off
  9. dissolutionthe residue was dissolved in 40 ml of water
  10. customthe end product was obtained by lyophilization
  11. customat 128° C.

Sources & evidence

ORD record
ord-d7a20ada732648f2bcbd8bf7815b632b
Source dataset
uspto-grants-1978_11
Patent number
US04125614

Reaction notes

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