Tetrahydrofuran → N-(3-Amino-2,5-dimethyl-4-thienyl)-N'-(2,6-dichlorophenyl)thiourea

HRID 349415Notes

Reaction equation

HRID 349415 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.[Cl:17][C:18]1[CH:23]=[CH:22][CH:21]=[C:20]([Cl:24])[C:19]=1[N:25]=[C:26]=[S:27]>C(N(CC)CC)C>[NH2:3][C:4]1[C:8]([NH:9][C:26]([NH:25][C:19]2[C:20]([Cl:24])=[CH:21][CH:22]=[CH:23][C:18]=2[Cl:17])=[S:27])=[C:7]([CH3:10])[S:6][C:5]=1[CH3:11]

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 1232391,3-Dichloro-2-isothiocyanatobenzeneHCID 693651873,4-Diamino-2,5-dimethylthiophene dihydrochloride

Product 1

HCID 86037737N-(3-Amino-2,5-dimethyl-4-thienyl)-N'-(2,6-dichlorophenyl)thiourea

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

A mixture of 0.5 g of 3,4-diamino-2,5-dimethylthiophene dihydrochloride, 30 ml of anhydrous THF and 0.49 g of triethylamine was stirred at room temperature for 30 minutes and then admixed with 0.569 g of 2,6-dichlorophenyl isothiocyanate. After the mixture had been heated to 40° C. for 30 minutes, it was stirred at room temperature for approx. 18 hours, the solvent was distilled off, the residue admixed with water and the precipitate filtered off and purified by column chromatography on silica gel using a mixture consisting of equal parts by volume of toluene and ethyl acetate. After the solvent had been distilled off, a foamy, amorphous product of m.p. 143–148° C. was obtained which, after melting, solidified again with a new m.p. of >300° C.

Workup

  1. temperatureAfter the mixture had been heated to 40° C. for 30 minutes
  2. stirringit was stirred at room temperature for approx. 18 hours
  3. distillationthe solvent was distilled off
  4. filtrationthe residue admixed with water and the precipitate filtered off
  5. custompurified by column chromatography on silica gel using a mixture
  6. distillationAfter the solvent had been distilled off
  7. customa foamy, amorphous product of m.p. 143–148° C. was obtained which

Sources & evidence

ORD record
ord-18776ac311d44c3e9c689a33402169f0
Source dataset
uspto-grants-2007_02
Patent number
US07179830B2

Reaction notes

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