Water → HCID 16785671, compound

HRID 493227Notes

Reaction equation

HRID 493227 reaction equation
[SH:1][C:2]1[N:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].Br.Br[CH2:13][C:14]1[CH:19]=[CH:18][N:17]=[CH:16][CH:15]=1.C(N(CC)CC)C.O>CN(C)C=O>[N:17]1[CH:18]=[CH:19][C:14]([CH2:13][S:1][C:2]2[C:3]([C:4]([OH:6])=[O:5])=[CH:7][CH:8]=[CH:9][N:10]=2)=[CH:15][CH:16]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 127522194-(Bromomethyl)pyridine hbrHCID 178524460HCID 178524460, compound

Product 1

HCID 16785671HCID 16785671, compoundYield 61%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2-Mercaptonicotinic acid (7.8 g, 50 mmol) and 4-(bromomethyl)pyridine hydrobromide (12.6 g, 50 mmol) were suspended in N,N-dimethylformamide (100 mL) under ice-cooling. Triethylamine (21 ml, 150 mmol) was added dropwise to the suspension, and the whole was stirred at room temperature for 6 hours. Water (300 mL) was added to the reaction mixture, then the aqueous layer was washed with ethyl acetate (100 mL). 2 N hydrochloric acid was added to the aqueous layer to adjust to pH 7, and the precipitated solid was filtered off. The solid was washed with water and diethyl ether, and dried at 50° C. under reduced pressure to give 7.5 g of the title reference compound as a gray solid. (Yield 61%)

Workup

  1. temperaturecooling
  2. washthe aqueous layer was washed with ethyl acetate (100 mL)
  3. addition2 N hydrochloric acid was added to the aqueous layer
  4. filtrationthe precipitated solid was filtered off
  5. washThe solid was washed with water and diethyl ether
  6. customdried at 50° C. under reduced pressure
  7. customto give 7.5 g of the title reference compound as a gray solid

Sources & evidence

ORD record
ord-f5938156d15747a5adbb354f145c71b4
Source dataset
uspto-grants-2009_05
Patent number
US07534802B2

Reaction notes

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