Triethylamine → HCID 19734410, compound

HRID 327030Notes

Reaction equation

HRID 327030 reaction equation
Cl[C:2]1[CH:7]=[CH:6][N:5]=[CH:4][C:3]=1[N+:8]([O-:10])=[O:9].[NH2:11][CH2:12][C:13]1[O:17][C:16]([CH2:18][OH:19])=[CH:15][CH:14]=1.C(N(CC)CC)C>ClC(Cl)Cl>[N+:8]([C:3]1[CH:4]=[N:5][CH:6]=[CH:7][C:2]=1[NH:11][CH2:12][C:13]1[O:17][C:16]([CH2:18][OH:19])=[CH:15][CH:14]=1)([O-:10])=[O:9]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 448213(5-(Aminomethyl)furan-2-yl)methanolHCID 27357814-Chloro-3-nitropyridine

Product 1

HCID 19734410HCID 19734410, compoundYield 71.3%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A mixture of 15.9 parts of 4-chloro-3-nitropyridine, 12.7 parts of 5-(aminomethyl)-2-furanmethanol, 13.3 parts of N,N-diethylethanamine and 745 parts of trichloromethane was stirred for 3 hours at reflux temperature. After cooling, the reaction mixture was washed with K2CO3 (aq.), dried, filtered and evaporated. The residue was crystallized from acetonitrile. The product was filtered off and dried, yielding 17.76 parts (71.3%) of 5-[[(3-nitro-4-pyridinyl)amino]methyl]-2-furanmethanol; mp. 134.9° C. (interm. 19).

Workup

  1. temperatureat reflux temperature
  2. temperatureAfter cooling
  3. washthe reaction mixture was washed with K2CO3 (aq.)
  4. customdried
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue was crystallized from acetonitrile
  8. filtrationThe product was filtered off
  9. customdried

Sources & evidence

ORD record
ord-c6842ccfa4b94c668dc806e66a80feac
Source dataset
uspto-grants-1993_12
Patent number
US05272150

Reaction notes

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