Ethyl isocyanate → HCID 69055710, compound

HRID 734649Notes

Reaction equation

HRID 734649 reaction equation
[CH2:1]([N:3]=[C:4]=[O:5])[CH3:2].CN(C1C=CC=CN=1)C.[NH2:15][C:16]1[NH:17][CH:18]=[C:19]([C:24]2[CH:29]=[CH:28][C:27]([N+:30]([O-:32])=[O:31])=[CH:26][CH:25]=2)[C:20]=1[C:21]([NH2:23])=[O:22]>O1CCCC1.O>[N+:30]([C:27]1[CH:26]=[CH:25][C:24]([C:19]2[C:20]([C:21]([NH2:23])=[O:22])=[C:16]([NH:15][C:4]([NH:3][CH2:1][CH3:2])=[O:5])[NH:17][CH:18]=2)=[CH:29][CH:28]=1)([O-:32])=[O:31]

Participants

6

Reactant 3

HCID 8022Ethyl isocyanateHCID 218852-DimethylaminopyridineHCID 57845538HCID 57845538, compound

Product 1

HCID 69055710HCID 69055710, compoundYield 46.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

0.074 cm3 (0.891 mmol) of ethyl isocyanate and 0.005 mg (0.040 mmol) of dimethylaminopyridine are added, at a temperature close to 25° C., to a solution of 0.2 g (0.81 mmol) of 2-amino-4-(4-nitrophenyl)-1H-pyrrole-3-carboxamide in 15 cm3 of tetrahydrofuran. After stirring for 16 hours at a temperature close to 60° C., the reaction medium is concentrated to dryness under reduced pressure (2.7 kPa) to give a residue which is stirred in 100 cm3 of water and then extracted with three times 50 cm3 of ethyl acetate. The organic phase is dried over anhydrous magnesium sulphate, filtered and concentrated to dryness under reduced pressure (2.7 kPa) to give a residue which is purified by flash chromatography [eluent: dichloromethane/methanol/acetonitrile (95/2.5/2.5 by volume)]. After concentrating the fractions under reduced pressure, 0.120 g of 4-(4-nitrophenyl)-2-(3-ethylureido)-1H-pyrrole-3-carboxamide is obtained in the form of a yellow powder. ES+: m/z=318 (MH+).

Workup

  1. customclose to 60° C.
  2. concentrationthe reaction medium is concentrated to dryness under reduced pressure (2.7 kPa)
  3. customto give a residue which
  4. extractionextracted with three times 50 cm3 of ethyl acetate
  5. dry with materialThe organic phase is dried over anhydrous magnesium sulphate
  6. filtrationfiltered
  7. concentrationconcentrated to dryness under reduced pressure (2.7 kPa)
  8. customto give a residue which
  9. customis purified by flash chromatography [eluent: dichloromethane/methanol/acetonitrile (95/2.5/2.5 by volume)]
  10. concentrationAfter concentrating the fractions under reduced pressure

Sources & evidence

ORD record
ord-30982ba9bb9946f49ceccd266cbecb1a
Source dataset
uspto-grants-2009_09
Patent number
US07592365B2

Reaction notes

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