Dimethylformamide → HCID 22966909, compound

HRID 2306000Notes

Reaction equation

HRID 2306000 reaction equation
[N:1]([CH2:4][CH2:5][CH3:6])=[C:2]=[S:3].CN(C)C=O.[NH2:12][C:13]1[S:14][CH:15]=[CH:16][C:17]=1[C:18]([O:20][CH3:21])=[O:19]>O>[CH2:4]([NH:1][C:2](=[S:3])[NH:12][C:13]1[S:14][CH:15]=[CH:16][C:17]=1[C:18]([O:20][CH3:21])=[O:19])[CH2:5][CH3:6]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 69403Propyl IsothiocyanateHCID 78381Methyl 2-amino-3-thenoate

Product 1

HCID 22966909HCID 22966909, compoundYield 40.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
132.5 °C

Procedure

In a sulfonation flask, 2.02 g (0.02 mol) of 1-isothiocynatopropane are added dropwise to 30 ml dimethylformamide and 3.0 g (0.019 mol) of methyl 2-aminothiophene-3-carboxylate. The reaction mixture is then stirred at 130-135° C. for 12 hours and after cooling added to 120 ml of water. The resulting mixture is then extracted three times with ethylacetate and the separated organic phase dried over sodium sulfate. The solvent is then removed in a water-jet vacuum, giving the crude product as a dark oil, which is purified by column chromatography over silica gel (eluant: tert.butylmethylether/hexane=2:3). 2.0 g of methyl 2-(3-propylthioureido)thiophene-3-carboxylate are obtained in the form of a yellow powder having a melting point of 122-124° C.

Workup

  1. temperatureafter cooling
  2. extractionThe resulting mixture is then extracted three times with ethylacetate
  3. dry with materialthe separated organic phase dried over sodium sulfate
  4. customThe solvent is then removed in a water-jet vacuum
  5. customgiving the crude product as a dark oil, which
  6. customis purified by column chromatography over silica gel (eluant: tert.butylmethylether/hexane=2:3)

Sources & evidence

ORD record
ord-301c832c24364a8789e8b94b397fcabb
Source dataset
uspto-grants-2002_08
Patent number
US06441169B1

Reaction notes

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