Sodium Bicarbonate → 5-cyano-N-[2-(4-hydroxy-2-methoxymethoxyphenyl)ethyl]-2-methoxybenzenesulfonamide

HRID 229584Notes

Reaction equation

HRID 229584 reaction equation
[NH2:1][CH2:2][CH2:3][C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][C:5]=1[O:11][CH2:12][O:13][CH3:14].C(=O)(O)[O-].[Na+].[C:20]([C:22]1[CH:23]=[CH:24][C:25]([O:32][CH3:33])=[C:26]([S:28](Cl)(=[O:30])=[O:29])[CH:27]=1)#[N:21]>O1CCCC1.O>[C:20]([C:22]1[CH:23]=[CH:24][C:25]([O:32][CH3:33])=[C:26]([S:28]([NH:1][CH2:2][CH2:3][C:4]2[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][C:5]=2[O:11][CH2:12][O:13][CH3:14])(=[O:30])=[O:29])[CH:27]=1)#[N:21]

Participants

6

Reactant 3

HCID 516892Sodium BicarbonateHCID 115287515-Cyano-2-methoxybenzene-1-sulfonyl chlorideHCID 178562194-(2-Aminoethyl)-3-methoxymethoxyphenol

Product 1

HCID 178562815-cyano-N-[2-(4-hydroxy-2-methoxymethoxyphenyl)ethyl]-2-methoxybenzenesulfonamideYield 89.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

4-(2-Aminoethyl)-3-methoxymethoxyphenol (12.3 g) and 7.9 g of sodium bicarbonate were suspended in a mixture of 133 mL of tetrahydrofuran and 14.4 mL of water, to the suspension was added 18 mL portions of a solution of 14.50 g of 5-cyano-2-methoxybenzenesulfonyl chloride in 180 mL of tetrahydrofuran every 10 minutes while the internal temperature was kept at 10-20° C. After being stirred at room temperature for 8 hours, the reaction mixture was purified by column chromatography on aminopropylated silica gel (eluent: ethyl acetate), and recrystallized from ethyl acetate-diisopropyl ether to give 21.87 g of 5-cyano-N-[2-(4-hydroxy-2-methoxymethoxyphenyl)ethyl]-2-methoxybenzenesulfonamide as a colorless crystal.

Workup

  1. customwas kept at 10-20° C
  2. customthe reaction mixture was purified by column chromatography on aminopropylated silica gel (eluent: ethyl acetate)
  3. customrecrystallized from ethyl acetate-diisopropyl ether

Sources & evidence

ORD record
ord-c763414b85e14974bc75aa3351b881fe
Source dataset
uspto-grants-2009_07
Patent number
US07563822B2

Reaction notes

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