Acetic Acid → 1-thioureido-1H-pyrrole-2-carboxamide

HRID 1685966Notes

Reaction equation

HRID 1685966 reaction equation
C([NH:9][C:10](=[S:20])[NH:11][N:12]1[CH:16]=[CH:15][CH:14]=[C:13]1[C:17]([NH2:19])=[O:18])(=O)C1C=CC=CC=1.C([O-])([O-])=O.[K+].[K+].CO.C(O)(=O)C>O.CC(C)=O>[NH:11]([N:12]1[CH:16]=[CH:15][CH:14]=[C:13]1[C:17]([NH2:19])=[O:18])[C:10]([NH2:9])=[S:20]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 887MethanolHCID 11430Potassium CarbonateHCID 100626351-(((Benzoylamino)thioxomethyl)amino)-1H-pyrrole-2-carboxamide

Product 1

HCID 104650001-thioureido-1H-pyrrole-2-carboxamideYield 79%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent

Procedure

Compound 1A (2.2 g, 7.6 mmol) was treated with a solution of K2CO3 (2.0 g, 14.8 mmol) in water (9 mL) at ambient temperature. Methyl alcohol (70 mL) and acetone (70 mL) were added and the mixture was heated to reflux for 18 hours. The reaction was cooled to ambient temperature and treated with acetic acid (2.0 mL, 35 mmol), and then concentrated to approximately 30 mL. The resulting suspension was cooled to 0° C. and the product was recovered by vacuum filtration to afford 1B (1.1 g, 79%). HPLC tR=0.405 min (YMC S5 Combiscreen ODS 4.6×50 mm, 10-90% aqueous methanol containing 0.2% H3PO4, 4 min gradient, monitored at 254 nm). 1H NMR (400 MHz, DMSO-d6) δ 10.4 (s, 1H), 8.13 (br s, 2H), 7.31 (br s, 1H), 7.10 (br s, 1H), 6.88 (t, 1H, J=2.0 Hz), 6.75 (dd, 1H, J=1.6, 4.0 Hz), 6.05 (t, 1H, J=3.6 Hz).

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux for 18 hours
  3. concentrationconcentrated to approximately 30 mL
  4. temperatureThe resulting suspension was cooled to 0° C.
  5. filtrationthe product was recovered by vacuum filtration

Sources & evidence

ORD record
ord-547bede71ccb4eb18ee166d62bdbd407
Source dataset
uspto-grants-2012_04
Patent number
US08148523B2

Reaction notes

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