Hydrochloric Acid → HCID 22630550, compound

HRID 2416371Notes

Reaction equation

HRID 2416371 reaction equation
Br[C:2]1[CH:10]=[C:9]([C:11]([OH:13])=[O:12])[C:8]([O:14][CH3:15])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[CH:16]1[C:28]2[NH:27][C:26]3[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=3)[C:20]=2[CH:19]=[CH:18][CH:17]=1.C([O-])([O-])=O.[K+].[K+].Cl>CN(C=O)C>[CH:25]1[C:26]2[N:27]([C:2]3[CH:10]=[C:9]([C:11]([OH:13])=[O:12])[C:8]([O:14][CH3:15])=[CH:7][C:3]=3[C:4]([OH:6])=[O:5])[C:28]3[C:20](=[CH:19][CH:18]=[CH:17][CH:16]=3)[C:21]=2[CH:22]=[CH:23][CH:24]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6854CarbazoleHCID 11430Potassium CarbonateHCID 277946HCID 277946, compound

Product 1

HCID 22630550HCID 22630550, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Into a three-neck flask, 10 g (3.6×10−2 mol) of 2-bromo-5-methoxyterephthalic acid prepared in the above step (2), 12.04 g (7×10−2 mmol, 2 eq) of carbazole, 12.94 g (9.4×10−2 mmol, 1.3 eq) of K2CO3 and 0.3 g (3% w/w) of Cu were introduced and reacted in the presence of 300 ml of DMF for 48 hours, then cooled to room temeparature. The used solvent was distilled off under reduced pressure and the aqueous solution was washed with water and diethyl ether several times. To the aqueous solution so obtained, 5 N HCl was slowly added to produce yellow precipitates, which were then recrystallized with CHCl3. Yield: 50% (6.5 g); m.p.: 298° C.

Workup

  1. additionwere introduced
  2. temperaturecooled to room temeparature
  3. distillationThe used solvent was distilled off under reduced pressure
  4. washthe aqueous solution was washed with water and diethyl ether several times
  5. customTo the aqueous solution so obtained
  6. customto produce yellow precipitates, which
  7. customwere then recrystallized with CHCl3

Sources & evidence

ORD record
ord-cce0f8a9a4974eb28a4944c908fc9d96
Source dataset
uspto-grants-2004_11
Patent number
US06824892B2

Reaction notes

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