1,1'-Carbonyldiimidazole → HCID 86667249, compound

HRID 2359917Notes

Reaction equation

HRID 2359917 reaction equation
[Br:1][C:2]1[N:7]=[C:6]([C:8]([OH:10])=O)[CH:5]=[CH:4][CH:3]=1.C(N1C=CN=C1)(N1C=CN=C1)=O.[CH3:23][S:24]([NH2:27])(=[O:26])=[O:25].C1(C2CCCCCCCCCC=2)CCCCCCCCNN=1>O1CCCC1>[Br:1][C:2]1[N:7]=[C:6]([C:8]([NH:27][S:24]([CH3:23])(=[O:26])=[O:25])=[O:10])[CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 682631,1'-CarbonyldiimidazoleHCID 72879MethanesulfonamideHCID 5939196-Bromopyridine-2-carboxylic acidHCID 536302743-(Cycloundecen-1-yl)-1,2-diazacycloundec-2-ene

Product 1

HCID 86667249HCID 86667249, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

5.40 g (26.7 mmol) of 6-bromo-2-pyridinecarboxylic acid were initially charged in 150 ml of tetrahydrofuran, 6.51 g (40.0 mmol) of carbonyldiimidazole were added and the mixture was boiled at reflux for 1 h. After cooling to room temperature, 3.81 g (40.0 mmol) of methanesulphonamide were added, the mixture was stirred for 10 min, then 6.10 g (40 mmol) of diazabicycloundecene (DBU) were added and the mixture was stirred at room temperature for 16 h.

Workup

  1. temperatureat reflux for 1 h
  2. stirringthe mixture was stirred at room temperature for 16 h.

Sources & evidence

ORD record
ord-d35c84e2a4ce4073bfc6b6f9b8aae008
Source dataset
uspto-grants-2014_04
Patent number
US08686004B2

Reaction notes

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