Methyl chloroformate → Methyl [6-(phenylsulfanyl)imidazo[1,2-a]pyridin-2-yl]carbamate

HRID 1447600Notes

Reaction equation

HRID 1447600 reaction equation
[NH2:1][C:2]1[N:3]=[C:4]2[CH:9]=[CH:8][C:7]([S:10][C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)=[CH:6][N:5]2[CH:17]=1.Cl[C:19]([O:21][CH3:22])=[O:20].C(=O)(O)[O-].[Na+]>O>[CH3:22][O:21][C:19]([NH:1][C:2]1[N:3]=[C:4]2[CH:9]=[CH:8][C:7]([S:10][C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)=[CH:6][N:5]2[CH:17]=1)=[O:20]

Participants

5

Reactant 3

HCID 6586Methyl chloroformateHCID 516892Sodium BicarbonateHCID 124108496-(Phenylsulfanyl)imidazo[1,2-a]pyridin-2-amine

Product 1

HCID 12414300Methyl [6-(phenylsulfanyl)imidazo[1,2-a]pyridin-2-yl]carbamate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

0.200 G. of 2-amino 6-(phenylthio) imidazo [1,2-a] pyridine is suspended in 2.2 ml. of water and treated dropwise with 0.0140 gm. of methyl chloroformate. After stirring the reaction mixture for 30 minutes at room temperature, solid sodium bicarbonate (0.111 gm.) is added in small portions. The solids are collected by filtration washed with water and dried. After recrystallization from ethanol, the purified 2-methoxycarbonylamino-6-(phenylthio) imidazo [1,2-a] pyridine m.p. 247°-249° C. is obtained.

Workup

  1. filtrationThe solids are collected by filtration
  2. washwashed with water
  3. customdried
  4. customAfter recrystallization from ethanol

Sources & evidence

ORD record
ord-e1c6055abde34c77a80bc8e4524be6a2
Source dataset
uspto-grants-1979_12
Patent number
US04177274

Reaction notes

Loading…