Pyridine → HCID 20130091, compound

HRID 845718Notes

Reaction equation

HRID 845718 reaction equation
[CH:1]1[CH:2]=[CH:3][C:4]2[N:9]=[C:8]([C:10]3[N:14]=[CH:13][S:12][CH:11]=3)[NH:7][C:5]=2[CH:6]=1.N1C=CC=CC=1.Cl[C:22]([O:24][CH2:25][Cl:26])=[O:23].[K+].[Br-]>C(Cl)(Cl)Cl>[Cl:26][CH2:25][O:24][C:22]([N:9]1[C:4]2[CH:3]=[CH:2][CH:1]=[CH:6][C:5]=2[N:7]=[C:8]1[C:10]1[N:14]=[CH:13][S:12][CH:11]=1)=[O:23]

Participants

6

Reactant 4

HCID 1049PyridineHCID 5430ThiabendazoleHCID 62754Chloromethyl chloroformateHCID 253877Potassium Bromide

Product 1

HCID 20130091HCID 20130091, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a suspension of 15.0 g of thiabendazole in 300 ml of chloroform, 6 g of pyridine was added and the suspension cooled in an ice bath. Chloromethyl chloroformate (10.6 g) was added to the reaction mixture dropwise during 10 minutes with stirring. A clear solution was formed which was kept stirred at room temperature for 16 hours. After washing the chloroform solution with water, it was dried over Na2SO4 and evaporated to a light yellow solid weighing 20.4 g. It was crystallized from EtOAc-CHCl3. Obtained in two crops were 15.07 g of compound, m.p. 143°-144° NMR (CDCl3) δ5.9 (2H, s, OCH2Cl), 7.2-8.2 (5H, m, aromatic), 8.93 (1H, d, J=3 Hz, aromatic). IR (KBr) ν3095, 1780, 1460, 1374, 1340, 1194, 1140, 1078 cm-1.

Workup

  1. additionwas added
  2. temperaturethe suspension cooled in an ice bath
  3. customA clear solution was formed which
  4. stirringwas kept stirred at room temperature for 16 hours
  5. washAfter washing the chloroform solution with water, it
  6. dry with materialwas dried over Na2SO4
  7. customevaporated to a light yellow solid
  8. customIt was crystallized from EtOAc-CHCl3
  9. customObtained in two crops

Sources & evidence

ORD record
ord-f05a5127a7a84c60adf828539b30a6e2
Source dataset
uspto-grants-1988_07
Patent number
US04760057

Reaction notes

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