Water → HCID 8403092, compound

HRID 458397Notes

Reaction equation

HRID 458397 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([S:9](Cl)(=[O:11])=[O:10])=[CH:5][CH:4]=1)#[N:2].[CH:13]1[CH:17]=[C:16]([CH2:18][NH2:19])[O:15][CH:14]=1.O>N1C=CC=CC=1>[C:1]([C:3]1[CH:8]=[CH:7][C:6]([S:9]([NH:19][CH2:18][C:16]2[O:15][CH:14]=[CH:13][CH:17]=2)(=[O:11])=[O:10])=[CH:5][CH:4]=1)#[N:2]

Participants

5

Reactant 3

HCID 962WaterHCID 3438FurfurylamineHCID 394974-Cyanobenzenesulfonyl chloride

Product 1

HCID 8403092HCID 8403092, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

4-Cyanobenzenesulfonyl chloride (1.77 g, 8.78 mmol) was dissolved in 8 mL of anhydrous pyridine and 2-furfurylamine (1.04 g, 9.66 mmol, 0.98 mL) was added. After 2 h, the reaction solutions were added to 100 mL cold water and stirred for 10 min. Filtration and washing with water provided the title compound as a yellow solid (2.04 g, 7.78 mmol, 89%). 1H NMR (300 MHz, CDCl3) δ 7.90 (d, J=8.4 Hz, 2H), 7.75 (d, J=8.4 Hz, 2H), 7.18 (s, 1H), 6.19 (m, 1H), 6.10 (m, 1H), 4.95 (m, 1H), 4.28 (d, J=6.0 Hz, 2H) ppm.

Workup

  1. filtrationFiltration
  2. washwashing with water

Sources & evidence

ORD record
ord-3e53e77fcca348d5bc90b8fcdfbb78ac
Source dataset
uspto-grants-2007_03
Patent number
US07189851B2

Reaction notes

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