Furfurylamine → HCID 13587967, compound

HRID 845769Notes

Reaction equation

HRID 845769 reaction equation
Cl[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N+:8]([O-:10])=[O:9].[O:11]1[CH:15]=[CH:14][CH:13]=[C:12]1[CH2:16][NH2:17].C(=O)([O-])O.[Na+].CN(C)C(=O)C>O>[N+:8]([C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[NH:17][CH2:16][C:12]1[O:11][CH:15]=[CH:14][CH:13]=1)([O-:10])=[O:9]

Participants

6

Reactant 4

HCID 3438FurfurylamineHCID 69451-Chloro-2-nitrobenzeneHCID 31374DimethylacetamideHCID 516892Sodium Bicarbonate

Product 1

HCID 13587967HCID 13587967, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of 15.7 parts of 1-chloro-2-nitrobenzene, 9.7 parts of 2-furanmethanamine, 8.4 parts of sodium hydrogen carbonate and 45 parts of N,N-dimethylacetamide was stirred overnight at about 120° C. The reaction mixture was cooled, water was added and the product was extracted with 1,1'-oxybisethane. The extract was dried, filtered and evaporated. The residue was purified by column-chromatography over silica gel using trichloromethane as eluent. The pure fractions were collected and the eluent was evaporated. The oily residue was triturated in petroleumether. The product was filtered off and dried, yielding 15 parts of N-(2-nitrophenyl)-2-furanmethanamine; mp. 85.6° C. (intermediate 1).

Workup

  1. temperatureThe reaction mixture was cooled
  2. extractionthe product was extracted with 1,1'-oxybisethane
  3. customThe extract was dried
  4. filtrationfiltered
  5. customevaporated
  6. customThe residue was purified by column-chromatography over silica gel
  7. customThe pure fractions were collected
  8. customthe eluent was evaporated
  9. customThe oily residue was triturated in petroleumether
  10. filtrationThe product was filtered off
  11. customdried

Sources & evidence

ORD record
ord-365a1a86740446fbb8847a4e21ea78aa
Source dataset
uspto-grants-1988_07
Patent number
US04760074

Reaction notes

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