Chloroform → 3-(Methoxycarbonylamino) 6-(2-pyridylthio) imidazo [1,2-a] pyridine

HRID 614852Notes

Reaction equation

HRID 614852 reaction equation
[NH2:1][C:2]1[N:6]2[CH:7]=[C:8]([S:11][C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][N:13]=3)[CH:9]=[CH:10][C:5]2=[N:4][CH:3]=1.C(Cl)(Cl)Cl.[CH3:22][O:23][C:24](Cl)=[O:25]>C(N(CC)CC)C>[CH3:22][O:23][C:24]([NH:1][C:2]1[N:6]2[CH:7]=[C:8]([S:11][C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][N:13]=3)[CH:9]=[CH:10][C:5]2=[N:4][CH:3]=1)=[O:25]

Participants

5

Reactant 3

HCID 6212ChloroformHCID 6586Methyl chloroformateHCID 542000433-Amino-6-(2-pyridylthio) imidazo [1,2-a] pyridine

Product 1

HCID 544713923-(Methoxycarbonylamino) 6-(2-pyridylthio) imidazo [1,2-a] pyridine

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

A solution of 1.0 g. of 3-amino-6-(2-pyridylthio) 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-(2-pyridylthio) imidazo [1,2-a] pyridine.

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-e11aeacb14794e068f7d70467db888d8
Source dataset
uspto-grants-1979_03
Patent number
US04146642

Reaction notes

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