4-Toluenesulfonyl chloride → 2-(5-Bromo-2-pyridinylamino)-1-cyanoethyl toluene-4-sulfonate

HRID 1792457Notes

Reaction equation

HRID 1792457 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([NH:8][CH2:9][CH:10]([OH:13])[C:11]#[N:12])=[N:6][CH:7]=1.C(N(C(C)C)CC)(C)C.[C:23]1([CH3:33])[CH:28]=[CH:27][C:26]([S:29](Cl)(=[O:31])=[O:30])=[CH:25][CH:24]=1.C(=O)(O)[O-].[Na+]>ClCCl>[C:23]1([CH3:33])[CH:28]=[CH:27][C:26]([S:29]([O:13][CH:10]([C:11]#[N:12])[CH2:9][NH:8][C:5]2[CH:4]=[CH:3][C:2]([Br:1])=[CH:7][N:6]=2)(=[O:31])=[O:30])=[CH:25][CH:24]=1

Participants

6

Reactant 4

HCID 73974-Toluenesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 516892Sodium BicarbonateHCID 220313423-(5-Bromo-2-pyridinylamino)-2-hydroxypropionitrile

Product 1

HCID 235374122-(5-Bromo-2-pyridinylamino)-1-cyanoethyl toluene-4-sulfonateYield 64.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

7.2 g of 3-(5-bromo-2-pyridinylamino)-2-hydroxypropionitrile was dissolved in 60 mL dichloromethane, and 7.8 mL diisopropyl ethylamine and 6.3 g of 4-toluenesulfonic acid chloride were added thereto, and while the temperature of the mixture was gradually increased to room temperature, the mixture was stirred for 2 hours. An aqueous saturated sodium bicarbonate solution was poured into the reaction mixture which was then extracted with ethyl acetate and washed with brine, then the organic layer was dried over anhydrous sodium sulfate, the solvent was removed, and the resulting crude product was purified by silica gel column chromatography (ethyl acetate/hexane) to give 7.64 g of the title compound (yellow oil).

Workup

  1. extractionwas then extracted with ethyl acetate
  2. washwashed with brine
  3. dry with materialthe organic layer was dried over anhydrous sodium sulfate
  4. customthe solvent was removed
  5. customthe resulting crude product was purified by silica gel column chromatography (ethyl acetate/hexane)

Sources & evidence

ORD record
ord-0dbdc9783d4d489ab198e2f789e8084b
Source dataset
uspto-grants-2006_07
Patent number
US07074801B1

Reaction notes

Loading…