Chloroform → Imidazo(1,2-a)pyridine

HRID 1447613Notes

Reaction equation

HRID 1447613 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 dimethylformamide-ethane 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 dimethylformamide-ethane

Sources & evidence

ORD record
ord-52d58b88a6cd4441b8d01a1b74a867d1
Source dataset
uspto-grants-1979_12
Patent number
US04177274

Reaction notes

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