2-Aminoethyl pyridine-3-carboxylate--hydrogen chloride (1/2) → N-(2-Fluoroethyl)-N'-[2-(3-pyridinecarbonyloxy)ethyl]-N-nitrosourea

HRID 359895Notes

Reaction equation

HRID 359895 reaction equation
Cl.Cl.[C:3]([O:11][CH2:12][CH2:13][NH2:14])(=[O:10])[C:4]1[CH:9]=[CH:8][CH:7]=[N:6][CH:5]=1.ClC1C=C(Cl)C(Cl)=CC=1[CH:24]([F:32])[CH2:25][N:26]([N:30]=[O:31])[C:27](=O)[O-:28].C(Cl)(Cl)Cl.C(OCC)(=O)C>N1C=CC=CC=1>[F:32][CH2:24][CH2:25][N:26]([N:30]=[O:31])[C:27]([NH:14][CH2:13][CH2:12][O:11][C:3]([C:4]1[CH:5]=[N:6][CH:7]=[CH:8][CH:9]=1)=[O:10])=[O:28]

Participants

5

Reactant 3

HCID 30711192-Aminoethyl pyridine-3-carboxylate--hydrogen chloride (1/2)HCID 21584013Chloroform ethylacetateHCID 867445092,4,5-trichlorophenyl-N-(2-fluoroethyl)-N-nitrosocarbamate

Product 1

HCID 15680048N-(2-Fluoroethyl)-N'-[2-(3-pyridinecarbonyloxy)ethyl]-N-nitrosourea

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution of 2-aminoethyl nicotinate dihydrochloride (1.5 g, 6.3 mmol) and 2,4,5-trichlorophenyl-N-(2-fluoroethyl)-N-nitrosocarbamate (2.18 g, 6.9 mmol) in 50 mL of pyridine was stirred under nitrogen at room temperature for 24 hours. The reaction was monitored by thin layer chromatography (silica, 1:1 chloroform/ethyl acetate, Rf 0.25). The solvent was removed in vacuo and the residue was chromatographed on a silica gel column by eluting, first with benzene to remove unreacted nitrosocarbamate and trichlorophenol, and then with chloroform to elute the desired product. The compound (1.56 g, 87.4%) melted at 75°-77° C. and was characterized by the structural formula: ##STR155##

Workup

  1. customThe solvent was removed in vacuo
  2. customthe residue was chromatographed on a silica gel column
  3. washby eluting, first with benzene
  4. customto remove unreacted nitrosocarbamate and trichlorophenol
  5. washwith chloroform to elute the desired product

Sources & evidence

ORD record
ord-7b3c4e86d9f4498e89761db54e23c16f
Source dataset
uspto-grants-1991_03
Patent number
US05002935

Reaction notes

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