Water → HCID 1019799, compound

HRID 2170598Notes

Reaction equation

HRID 2170598 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 5 (7.5 g, 33 mmol), 2-bromoaniline (5.86 g, 33 mmol) and triethylamine (14 mL, 100 mmol) in anhydrous dichloromethane (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 concentrated to 150 mL, white crystalline solid was crashed out. Filtration and washing with hexanes gave a white solid 6 (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 concentrated to 150 mL, white crystalline solid
  5. filtrationFiltration
  6. washwashing with hexanes

Sources & evidence

ORD record
ord-0c0b2f5a5f6e4a59bb860e1af287adfe
Source dataset
uspto-grants-2015_06
Patent number
US09051284B2

Reaction notes

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