Formamide → HCID 178468549, compound

HRID 369865Notes

Reaction equation

HRID 369865 reaction equation
[NH2:1][C:2]1[NH:3][C:4]([C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:5][C:6]=1[C:7](OCC)=[O:8].[CH:17]([NH2:19])=O.CN(C=O)C>C(O)=O>[CH2:15]([O:14][C:12]([C:4]1[NH:3][C:2]2[N:1]=[CH:17][N:19]=[C:7]([OH:8])[C:6]=2[CH:5]=1)=[O:13])[CH3:16]

Participants

5

Reactant 3

HCID 713FormamideHCID 6228DimethylformamideHCID 21262628diethyl 5-amino-1H-pyrrole-2,4-dicarboxylate

Product 1

HCID 178468549HCID 178468549, compound

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Conditions

Temperature
2.5 °C

Procedure

With the exclusion of air, 51.5 g (227 mmol) of 2-amino-3,5-bis(ethoxycarbonyl)-1H-pyrrole, 455 ml of formamide, 227 ml of DMF and 113 ml of formic acid are stirred at 140° C. for 27 hours. The resulting yellow suspension is cooled to 0-5° C. Filtering and washing with isopropanol and hexane yield the title compound; 1H-NMR (DMSO-d6): 13-12 (2 HX), 7.99 and 7.11 (2s, 2H), 4.31 (q, J=7, 2H), 1.32 (t, J=7, 3H).

Workup

  1. filtrationFiltering
  2. washwashing with isopropanol and hexane

Sources & evidence

ORD record
ord-09866984ab5047afae57d5be42ed1f88
Source dataset
uspto-grants-2000_10
Patent number
US06140332

Reaction notes

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