2-Amino-5-bromopyridine → HCID 15591382, compound

HRID 1905643Notes

Reaction equation

HRID 1905643 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([Br:8])=[CH:4][N:3]=1.[C:9]1([S:15]([C:18]([S:23]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)(=[O:25])=[O:24])=[CH:19]OCC)(=[O:17])=[O:16])[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1>C1(C)C=CC=CC=1>[C:9]1([S:15]([C:18]([S:23]([C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=2)(=[O:25])=[O:24])=[CH:19][NH:1][C:2]2[CH:7]=[CH:6][C:5]([Br:8])=[CH:4][N:3]=2)(=[O:16])=[O:17])[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1

Participants

4

Reactant 2

HCID 706222-Amino-5-bromopyridineHCID 124009381,1-Bis(phenylsulphonyl)-2-ethoxyethene

Product 1

HCID 15591382HCID 15591382, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 2-amino-5-bromopyridine (38 g) and 1,1-bis(phenylsulphonyl)-2-ethoxyethene [70 g; prepared as described by Stetter et al, Monatshefte fur Chemie, 103, 1262-1270 (1972)] in toluene (1 liter) was slowly distilled during a period of 2 hours, maintaining the volume approximately constant by the gradual addition of further toluene to replace the liquid removed by the distillation. The mixture was then concentrated under vacuum and the residue was recrystallised twice from a mixture of chloroform and ethanol, to give 1,1-bis(phenylsulphonyl)-2-(5-bromopyrid-2-ylamino)ethene (80 g) m.p. 177°-179° C.

Workup

  1. distillationwas slowly distilled during a period of 2 hours
  2. temperaturemaintaining the volume
  3. additionapproximately constant by the gradual addition of further toluene
  4. customremoved by the distillation
  5. concentrationThe mixture was then concentrated under vacuum
  6. customthe residue was recrystallised twice from a mixture of chloroform and ethanol

Sources & evidence

ORD record
ord-8c4ba6ce3c914df7a1092da4c877274b
Source dataset
uspto-grants-1987_03
Patent number
US04647569

Reaction notes

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