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

HRID 1732464Notes

Reaction equation

HRID 1732464 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-004de32728e4451d9e50f5c67cac711e
Source dataset
uspto-grants-1980_12
Patent number
US04237300

Reaction notes

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