Chloroform → Imidazo(1,2-a)pyridine

HRID 1732478Notes

Reaction equation

HRID 1732478 reaction equation
N[C:2]1[N:6]2[CH:7]=[C:8](SC3C=CC=CC=3)[CH:9]=[CH:10][C:5]2=[N:4][CH:3]=1.C(Cl)(Cl)Cl.COC(Cl)=O>C(N(CC)CC)C>[N:4]1[CH:3]=[CH:2][N:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=12

Participants

5

Reactant 3

HCID 6212ChloroformHCID 6586Methyl chloroformateHCID 53813641HCID 53813641, compound

Product 1

HCID 78960Imidazo(1,2-a)pyridine

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

A solution of 1.0 g. of 3-amino-6-(phenylthio)imidazo [1,2-a] pyridine in 25 ml. of chloroform containing 0.401 g. of triethyl amine is treated dropwise with 0.378 g. of methylchloroformate. The reaction mixture is stirred for 3 hours at room temperature. The chloroform is removed in vacuo and the residue is triturated with water. The solids are collected by filtration, washed well with water and dried. Recrystallization from dimethylformamideethane yields pure 3-(methoxycarbonylamino) 6-phenylthio)imidazo [1,2-a] pyridine m.p. 211°-215° C.

Workup

  1. customThe chloroform is removed in vacuo
  2. customthe residue is triturated with water
  3. filtrationThe solids are collected by filtration
  4. washwashed well with water
  5. customdried
  6. customRecrystallization from dimethylformamideethane

Sources & evidence

ORD record
ord-a6fc43047fe54e36a650939596aa90e8
Source dataset
uspto-grants-1980_12
Patent number
US04237300

Reaction notes

Loading…