Chloroform → HCID 178440586, compound

HRID 351409Notes

Reaction equation

HRID 351409 reaction equation
[C:1]([C:5]1[CH:9]=[C:8]([C:10](OCC)=[O:11])[N:7]([NH2:15])[CH:6]=1)([CH3:4])([CH3:3])[CH3:2].C(O)(=O)C.[CH:20](N)=[NH:21].C(OC(O)C)C.C(Cl)(Cl)Cl>CO>[C:1]([C:5]1[CH:9]=[C:8]2[N:7]([CH:6]=1)[N:15]=[CH:20][N:21]=[C:10]2[OH:11])([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 6212ChloroformHCID 160693Formamidine acetateHCID 101298981-EthoxyethanolHCID 21075143HCID 21075143, compound

Product 1

HCID 178440586HCID 178440586, compoundYield 25.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Ethyl 3-tert-Butyl-1-aminopyrrole-5-carboxylate (1.00 g, 4.76 mmol, 1 eq), formamidine acetate (1.46 g, 14.3 mmol, 3 eq.) and ethoxyethanol (10 mL) were mixed and refluxed for 3 hours. The solvent was stripped and then restripped from chloroform (3×) to yield a solid. This solid was stirred in 5 mL MeOH, filtered, and the collected solids rinsed with Et2O and dried to yield 233 mg of a white solid as product. LCMS found: (M+H)++=191.

Workup

  1. temperaturerefluxed for 3 hours
  2. customto yield a solid
  3. filtrationfiltered
  4. washthe collected solids rinsed with Et2O
  5. customdried

Sources & evidence

ORD record
ord-ed81184dd52d480cbfa4fcd39e541968
Source dataset
uspto-grants-2007_02
Patent number
US07183270B2

Reaction notes

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