Water → HCID 1019799, compound

HRID 2041800Notes

Reaction equation

HRID 2041800 reaction equation
[Br:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([CH:10]=1)[C:7](Cl)=[O:8].[Br:11][C:12]1[CH:18]=[CH:17][CH:16]=[CH:15][C:13]=1[NH2:14].C(N(CC)CC)C.O>ClCCl>[Br:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([CH:10]=1)[C:7]([NH:14][C:13]1[CH:15]=[CH:16][CH:17]=[CH:18][C:12]=1[Br:11])=[O:8]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 119922-BromoanilineHCID 27812235-Bromonicotinoyl chloride

Product 1

HCID 1019799HCID 1019799, compoundYield 85.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 5-bromonicotinoyl chloride (3) (7.5 g, 33 mmol), 2-bromoaniline (5.86 g, 33 mmol) and triethylamine (NEt3) (14 mL, 100 mmol) in anhydrous dichlormethane (DCM) (100 mL) was stirred under argon overnight. The resulting mixture was worked up with water and extracted with dichloromethane (200 mL×2). The organic phase was collected and dried over Na2SO4. After concentrating to 150 mL, a white crystalline solid was crashed precipitated out. Filtration and washing with hexanes gave a white solid 4 (10.0 g, 85% yield).

Workup

  1. extractionextracted with dichloromethane (200 mL×2)
  2. customThe organic phase was collected
  3. dry with materialdried over Na2SO4
  4. concentrationAfter concentrating to 150 mL
  5. customa white crystalline solid was crashed precipitated out
  6. filtrationFiltration
  7. washwashing with hexanes

Sources & evidence

ORD record
ord-6b5a1ad25a264b4f907ca04c51124895
Source dataset
uspto-grants-2013_11
Patent number
US08585926B2

Reaction notes

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