methyl N-(2-chloroacetyl)carbamate → 6-(Methylthio)imidazo[1,2-a]pyridine-2-carbamic acid, methyl ester

HRID 27412Notes

Reaction equation

HRID 27412 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([S:8][CH3:9])=[CH:4][N:3]=1.[CH3:10][O:11][C:12](=[O:18])[NH:13][C:14](=O)[CH2:15]Cl>CN(P(N(C)C)(N(C)C)=O)C>[CH3:9][S:8][C:5]1[CH:6]=[CH:7][C:2]2[N:3]([CH:15]=[C:14]([NH:13][C:12]([O:11][CH3:10])=[O:18])[N:1]=2)[CH:4]=1

Participants

4

Reactant 2

HCID 518783methyl N-(2-chloroacetyl)carbamateHCID 151797975-(Methylsulfanyl)pyridin-2-amine

Product 1

HCID 867372006-(Methylthio)imidazo[1,2-a]pyridine-2-carbamic acid, methyl ester

Reagents, catalysts & solvents 1

HCID 12679HexamethylphosphoramideSolvent

Conditions

Temperature
100 °C

Procedure

A suspension of 2-amino-5-(methylthio)pyridine (0.667 mol) and methyl(chloroacetyl)carbamate (0.667 mol) in 325 ml of HMPT is heated at 100° C. for 5 hours. After dilution with 2000 ml of H2O, the product is collected by filtration, successively washed with H2O, MeOH and CH2Cl2, and dried.

Workup

  1. filtrationAfter dilution with 2000 ml of H2O, the product is collected by filtration
  2. washsuccessively washed with H2O, MeOH and CH2Cl2
  3. customdried

Sources & evidence

ORD record
ord-c727c9887d654ab193b8d135c22c6424
Source dataset
uspto-grants-1980_09
Patent number
US04221796

Reaction notes

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