Tetrahydrofuran → N-(3-Amino-2,5-dimethyl-4-thienyl)-N'-(4-methyl-3-thienyl)thiourea

HRID 349417Notes

Reaction equation

HRID 349417 reaction equation
Cl.Cl.[NH2:3][C:4]1[C:8]([NH2:9])=[C:7]([CH3:10])[S:6][C:5]=1[CH3:11].C1COCC1.[CH3:17][C:18]1[C:19]([N:23]=[C:24]=[S:25])=[CH:20][S:21][CH:22]=1>C(N(CC)CC)C>[NH2:3][C:4]1[C:8]([NH:9][C:24]([NH:23][C:19]2[C:18]([CH3:17])=[CH:22][S:21][CH:20]=2)=[S:25])=[C:7]([CH3:10])[S:6][C:5]=1[CH3:11]

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 221398273-Isothiocyanato-4-methylthiopheneHCID 693651873,4-Diamino-2,5-dimethylthiophene dihydrochloride

Product 1

HCID 86037740N-(3-Amino-2,5-dimethyl-4-thienyl)-N'-(4-methyl-3-thienyl)thiourea

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

A mixture of 1 g of 3,4-diamino-2,5-dimethylthiophene dihydrochloride, 60 ml of anhydrous THF and 1.05 g of triethylamine was stirred at room temperature for 30 minutes and then admixed with 0.902 g of 4-methyl-3-thienyl isothiocyanate. After the mixture had been heated to 35–40° C. for 15 minutes, it was stirred for approx. 18 hours, the solvent was distilled off and the residue was admixed with water and extracted repeatedly with ethyl acetate. After the solvent of the combined organic phases had been distilled off, the residue was purified by column chromatography on silica gel using a solvent mixture of equal parts of toluene and ethyl acetate. After the solvent had been distilled off under reduced pressure, a semicrystalline oil was obtained and was used without further purification.

Workup

  1. temperatureAfter the mixture had been heated to 35–40° C. for 15 minutes
  2. stirringit was stirred for approx. 18 hours
  3. distillationthe solvent was distilled off
  4. extractionextracted repeatedly with ethyl acetate
  5. distillationAfter the solvent of the combined organic phases had been distilled off
  6. customthe residue was purified by column chromatography on silica gel using
  7. additiona solvent mixture of equal parts of toluene and ethyl acetate
  8. distillationAfter the solvent had been distilled off under reduced pressure
  9. customa semicrystalline oil was obtained
  10. customwas used without further purification

Sources & evidence

ORD record
ord-2d73ffda6def4ecfb17821542341df67
Source dataset
uspto-grants-2007_02
Patent number
US07179830B2

Reaction notes

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