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

HRID 359893Notes

Reaction equation

HRID 359893 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]([Cl: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>[Cl: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 867445052,4,5-trichlorophenyl-N(2-chloroethyl)-N-nitrosocarbamate

Product 1

HCID 15680044N-(2-Chloroethyl)-N'-[2-(3-pyridinecarbonyloxy)ethyl]-N-nitrosourea

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution of 2-aminoethyl nicotinate dihydrochloride (1.25 g, 52 mmol) and 2,4,5-trichlorophenyl-N-(2-chloroethyl)-N-nitrosocarbamate (2 g, 6 mmol) in 40 mL of pyridine was stirred under nitrogen at room temperature for 24 hours. The reaction was monitored by thin layer chromatography (silica, 1:1 chloro form/ethyl acetate, Rf 0.26). 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 by-product, and then with chloroform, to give the desired product. The resultant oil solidified in the freezer. It melted at 63°-64° C. and had the formula ##STR152##

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 by-product

Sources & evidence

ORD record
ord-ff28e2adbcf34efdb965e629e34b684f
Source dataset
uspto-grants-1991_03
Patent number
US05002935

Reaction notes

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