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

HRID 461197
Notes
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Reaction equation

HRID 461197 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]
ParticipantsProcedureWorkupSources & evidenceReaction notes

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 3283
Diethyl Ether
Solvent

Procedure

6.8 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=N1615 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-88cfa64fe19a4ffcab3a66d6a399d3d7
Source dataset
uspto-grants-1977_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04061761

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes