Diisopropylethylamine → N-(3-amino-4-thienyl)-N'-(4-methyl-3-thienyl)thiourea

HRID 349412Notes

Reaction equation

HRID 349412 reaction equation
Cl.Cl.[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.[CH3:19][C:20]1[C:21]([N:25]=[C:26]=[S:27])=[CH:22][S:23][CH:24]=1>O1CCCC1>[NH2:3][C:4]1[C:8]([NH:9][C:26]([NH:25][C:21]2[C:20]([CH3:19])=[CH:24][S:23][CH:22]=2)=[S:27])=[CH:7][S:6][CH:5]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 127073423,4-Diaminothiophene dihydrochlorideHCID 221398273-Isothiocyanato-4-methylthiophene

Product 1

HCID 86037734N-(3-amino-4-thienyl)-N'-(4-methyl-3-thienyl)thiourea

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 1.87 g of 3,4-diaminothiophene dihydrochloride, 60 ml of anhydrous tetrahydrofuran (THF) and 2.58 g of N-ethyl-N,N-diisopropylamine was stirred at room temperature for 30 minutes and then admixed with 1.5 g of 4-methyl-3-thienyl isothiocyanate. After stirring over approx. 18 hours, the solvent was distilled off, the residue admixed with water and extracted repeatedly with ethyl acetate. After the combined organic phases had been treated with activated carbon, they were dried over sodium sulfate and the solvent was once again distilled off. The N-(3-amino-4-thienyl)-N′-(4-methyl-3-thienyl)thiourea was obtained as an amorphous foamy solid.

Workup

  1. stirringAfter stirring over approx. 18 hours
  2. distillationthe solvent was distilled off
  3. extractionthe residue admixed with water and extracted repeatedly with ethyl acetate
  4. additionAfter the combined organic phases had been treated with activated carbon, they
  5. dry with materialwere dried over sodium sulfate
  6. distillationthe solvent was once again distilled off

Sources & evidence

ORD record
ord-b42dad8b0c4d4bada62dd01825bed579
Source dataset
uspto-grants-2007_02
Patent number
US07179830B2

Reaction notes

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