Hydrochloric Acid → HCID 11535906, compound

HRID 536084Notes

Reaction equation

HRID 536084 reaction equation
C(O[C:4]([N:6]=[C:7]=[S:8])=[O:5])C.C(OC([C:14]1[NH:15][CH:16]=[CH:17][C:18]=1[NH:19][CH2:20][CH2:21][CH2:22][CH3:23])=O)C.[OH-].[K+].Cl>C1(C)C=CC=CC=1.O>[CH2:20]([N:19]1[C:18]2[CH:17]=[CH:16][NH:15][C:14]=2[C:7](=[S:8])[NH:6][C:4]1=[O:5])[CH2:21][CH2:22][CH3:23]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 85320Ethyl isothiocyanatoformateHCID 67068503HCID 67068503, compound

Product 1

HCID 11535906HCID 11535906, compoundYield 6.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Conditions

Temperature
90 °C

Procedure

Ethoxycarbonyl isothiocyanate (0.13 ml, 1.1 mmol) was added to 3-(butylamino)-1H-pyrrole-2-carboxylic acid ethyl ester (0.23 g, 1.1 mmol) in toluene (5 mL) and the mixture was heated at 90° C. for 1 h. The precipitate was filtered off and washed with hexane. The intermediate product was treated with potassium hydroxide (0.55 g, 9.9 mmol) in water (9 mL), and heated to reflux for 15 h. After cooling to ambient temperature, the pH was adjusted to pH 5 with 12 M HCl. The resultant precipitate was collected by filtration and washed with water. The crude product was purified using preparative HPLC to give the title compound (16 mg, 6%) as a solid.

Workup

  1. filtrationThe precipitate was filtered off
  2. washwashed with hexane
  3. temperatureheated
  4. temperatureto reflux for 15 h
  5. temperatureAfter cooling to ambient temperature
  6. filtrationThe resultant precipitate was collected by filtration
  7. washwashed with water
  8. customThe crude product was purified

Sources & evidence

ORD record
ord-14cf1d5d6a6d41e2a083274dd96d90cb
Source dataset
uspto-grants-2014_10
Patent number
US08859568B2

Reaction notes

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