Chloroform → HCID 53743984, compound

HRID 2420108Notes

Reaction equation

HRID 2420108 reaction equation
[CH2:1]([C:8]1[CH:9]=[CH:10][C:11]([C:14]([OH:16])=O)=[N:12][CH:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(Cl)(Cl)Cl.C(Cl)(=O)OCC.[CH2:27]([NH2:29])[CH3:28]>O.C(N(CC)CC)C>[CH2:27]([NH:29][C:14](=[O:16])[C:11]1[CH:10]=[CH:9][C:8]([CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)=[CH:13][N:12]=1)[CH3:28]

Participants

7

Reactant 4

HCID 6212ChloroformHCID 6341EthylamineHCID 10928Ethyl chloroformateHCID 30428422-Pyridinecarboxylic acid, 5-(phenylmethyl)-

Product 1

HCID 53743984HCID 53743984, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8471TriethylamineSolvent

Procedure

2.1 Grams of 5-benzylpicolinic acid were dissolved in 20 ml. of chloroform. The resulting solution was then added with 1.2 g of triethylamine and 1.1 g of ethyl chlorocarbonate and thereafter with 33% ethylamine solution dropwise under ice-cooling and stirring. After 30 minutes 10 ml. of water were added thereto and the mixture was fractionated. The organic layer was washed with 10% aqueous ammonia. After drying, the solvent was distilled out. The residue was recrystallized from n-hexane to obtain 2.0 g of 5-benzyl-picolinic acid N-ethylamide as colorless crystals of a melting point of 77°~78° C.

Workup

  1. washThe organic layer was washed with 10% aqueous ammonia
  2. customAfter drying
  3. distillationthe solvent was distilled out
  4. customThe residue was recrystallized from n-hexane

Sources & evidence

ORD record
ord-ca175ef5fc3b44cc8c2241de870bf24d
Source dataset
uspto-grants-1978_08
Patent number
US04109000

Reaction notes

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