Diisopropylethylamine → N-(4-amino-3-thienyl)-N'-(2-chloro-4-methylthienyl)thiourea

HRID 349420Notes

Reaction equation

HRID 349420 reaction equation
Br.Br.[NH2:3][C:4]1[C:8]([NH2:9])=[CH:7][S:6][CH:5]=1.C(N(C(C)C)C(C)C)C.[Cl:19][C:20]1[S:21][CH:22]=[C:23]([CH3:28])[C:24]=1[N:25]=[C:26]=[S:27]>C1COCC1>[NH2:9][C:8]1[C:4]([NH:3][C:26]([NH:25][C:24]2[C:23]([CH3:28])=[CH:22][S:21][C:20]=2[Cl:19])=[S:27])=[CH:5][S:6][CH:7]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 132679662-Chloro-4-methyl-3-thienyl isothiocyanateHCID 21989329Thiophene-3,4-diamine dihydrobromide

Product 1

HCID 86037741N-(4-amino-3-thienyl)-N'-(2-chloro-4-methylthienyl)thiourea

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

0.55 g of 3,4-diaminothiophene dihydrobromide was added to a solution of 0.51 g of N-ethyl-N,N-diisopropylamine in 30 ml of anhydrous THF, the mixture was stirred at room temperature for approx. 5 minutes and the solution was then admixed with a mixture of 0.4 g of 2-chloro-4-methyl-3-thienyl isothiocyanate in 5 ml of THF. The mixture was stirred at room temperature for 3 hours and at 40° C. for 10 minutes. After it had been left to stand overnight, the solvent was distilled off, and the residue was treated with water and extracted with ethyl acetate. The insoluble fraction was filtered off, and the organic phase was washed with water and dried over sodium sulfate. After the solvent had been distilled off, the product was purified by column chromatography on silica gel using a mixture of 1 part by volume of toluene and 1 part by volume of ethyl acetate and, after the solvent had been distilled off, the N-(4-amino-3-thienyl)-N′-(2-chloro-4-methylthienyl)thiourea was obtained as a crystalline solid.

Workup

  1. stirringThe mixture was stirred at room temperature for 3 hours and at 40° C. for 10 minutes
  2. waitAfter it had been left
  3. waitto stand overnight
  4. distillationthe solvent was distilled off
  5. additionthe residue was treated with water
  6. extractionextracted with ethyl acetate
  7. filtrationThe insoluble fraction was filtered off
  8. washthe organic phase was washed with water
  9. dry with materialdried over sodium sulfate
  10. distillationAfter the solvent had been distilled off
  11. customthe product was purified by column chromatography on silica gel using
  12. additiona mixture of 1 part by volume of toluene and 1 part by volume of ethyl acetate
  13. distillationafter the solvent had been distilled off

Sources & evidence

ORD record
ord-a9d150185ad54c57af4c8db0d51772ca
Source dataset
uspto-grants-2007_02
Patent number
US07179830B2

Reaction notes

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