Hydrochloric Acid → HCID 17312872, compound

HRID 240824Notes

Reaction equation

HRID 240824 reaction equation
[CH2:1]([N:3]=[C:4]=[S:5])[CH3:2].[S:6]1[CH:10]=[CH:9][CH:8]=[C:7]1[CH2:11][CH2:12][NH2:13].C(N(CC)CC)C.Cl>ClCCl.O>[CH2:1]([NH:3][C:4]([NH:13][CH2:12][CH2:11][C:7]1[S:6][CH:10]=[CH:9][CH:8]=1)=[S:5])[CH3:2]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 10966Ethyl isothiocyanateHCID 116521Thiopheneethanamine

Product 1

HCID 17312872HCID 17312872, compoundYield 89%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

Ethyl isothiocyanate (1.3 g, 15.0 mmol) was slowly added dropwise to a solution of thiopheneethylamine (1.3 g, 10.2 mmol) in dichloromethane (150 mL). Triethyl amine (3.8 mL, 20.4 mmol) was added dropwise to the mixture and stirred at room temperature for 2 h. After completion of the reaction, pH of the resulting solution was adjusted to about 7 using aqueous 1N HCl, to which water was added. The resulting mixture was extracted with dichloromethane. The residue was purified by flash column chromatography (ethyl acetate:hexanes=1:3), to give the title compound (1.9 g, 89%).

Workup

  1. customAfter completion of the reaction, pH of the resulting solution
  2. additionwas added
  3. extractionThe resulting mixture was extracted with dichloromethane
  4. customThe residue was purified by flash column chromatography (ethyl acetate:hexanes=1:3)

Sources & evidence

ORD record
ord-98e5c6d562f14ff2983755fa2a3af0c9
Source dataset
uspto-grants-2014_02
Patent number
US08648111B2

Reaction notes

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