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

HRID 2419318Notes

Reaction equation

HRID 2419318 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-a31f27c2d3d64613a057e975e573bbba
Source dataset
uspto-grants-1978_08
Patent number
US04105767

Reaction notes

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