Ethyl chloroformate → HCID 20331700, compound

HRID 1112314Notes

Reaction equation

HRID 1112314 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Br:8])[N:3]=1.Cl[C:10]([O:12][CH2:13][CH3:14])=[O:11]>N1C=CC=CC=1>[CH2:13]([O:12][C:10]([NH:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Br:8])[N:3]=1)=[O:11])[CH3:14]

Participants

4

Reactant 2

HCID 10928Ethyl chloroformateHCID 3008092-Amino-6-bromopyridine

Product 1

HCID 20331700HCID 20331700, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

10.0 g (0.0578 mole) of 2-amino-6-bromopyridine was dissolved in 40 ml dry pyridine and 6.4 ml (0.067 mole) of ethyl chloroformate was added dropwise while the solution was stirred and cooled in an ice-bath to maintain the reaction temperature at 15°-18° C. After 4 hours at room temperature, the reaction mixture was poured into 150 ml of ice water and kept at 0° C overnight. Impure 2-ethoxycarbonylamino-6-bromopyridine was obtained by filtration and subsequently recrystallized from 2:1 methanol-water solution, giving an 88% yield of white solid, m.p.=70.2°-71.0° C.

Workup

  1. temperaturecooled in an ice-bath
  2. temperatureto maintain the reaction temperature at 15°-18° C
  3. waitkept at 0° C overnight

Sources & evidence

ORD record
ord-6111211db7e24bba8245552905c0a51c
Source dataset
uspto-grants-1978_10
Patent number
US04122084

Reaction notes

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