2-Amino-5-bromopyridine → HCID 86753004, compound

HRID 481947Notes

Reaction equation

HRID 481947 reaction equation
[Cl:1][C:2](OCC(Cl)(Cl)Cl)=[O:3].[NH2:10][C:11]1[CH:16]=[CH:15][C:14]([Br:17])=[CH:13][N:12]=1>ClCCCl>[ClH:1].[Br:17][C:14]1[CH:15]=[CH:16][C:11]([N:10]=[C:2]=[O:3])=[N:12][CH:13]=1

Participants

4

Reactant 2

HCID 706222-Amino-5-bromopyridineHCID 870632,2,2-Trichloroethyl chloroformate

Product 1

HCID 86753004HCID 86753004, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

78.0 ml (0.64 mol) of trichloroethyl chloroformate are added dropwise at boiling heat to a stirred solution of 100 g (0.58 mol) of 2-amino-5-bromopyridine in 400 ml of 1,2-dichloroethane. After the addition the mixture is refluxed for 2 h, then it may be cooled to room temperature. The resulting precipitate is removed by filtration, washed well with 100 ml of 1,2-dichloroethane and dried over sodium hydroxide in a high vacuum. 98.3 g (72%) of the title compound are obtained as a yellow solid.

Workup

  1. additionAfter the addition the mixture
  2. temperatureis refluxed for 2 h
  3. customThe resulting precipitate is removed by filtration
  4. washwashed well with 100 ml of 1,2-dichloroethane
  5. dry with materialdried over sodium hydroxide in a high vacuum

Sources & evidence

ORD record
ord-16f3e76f232b4595a87974f55596f7ed
Source dataset
uspto-grants-1998_08
Patent number
US05792765

Reaction notes

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