4-Toluenesulfonyl chloride → HCID 56980661, compound

HRID 2121151Notes

Reaction equation

HRID 2121151 reaction equation
Cl.[NH:2]1[CH:6]=[C:5]([CH2:7][C:8]([OH:10])=[O:9])[N:4]=[CH:3]1.[C:11]1([CH3:21])[CH:16]=[CH:15][C:14]([S:17](Cl)(=[O:19])=[O:18])=[CH:13][CH:12]=1>[OH-].[Na+].O>[C:11]1([CH3:21])[CH:16]=[CH:15][C:14]([S:17]([N:2]2[CH:6]=[C:5]([CH2:7][C:8]([OH:10])=[O:9])[N:4]=[CH:3]2)(=[O:19])=[O:18])=[CH:13][CH:12]=1

Participants

5

Reactant 2

HCID 73974-Toluenesulfonyl chlorideHCID 178479752HCID 178479752, compound

Product 1

HCID 56980661HCID 56980661, compoundYield 63%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 14798Sodium HydroxideSolvent3×

Procedure

To a solution of 4-imidazole acetic acid hydrochloride (1 g, 6.15 mmol) in 6.2 mL of 1 N NaOH and 18 mL of water was added 4-toluenesulfonyl chloride (1.29 g, 6.77 mmol) and the mixture was stirred at ambient temperature. The pH of the mixture was maintained at 8.5 by addition of 1 N NaOH. After 3 hours, a total volume of 12 mL of 1 N NaOH was added and a clear solution was obtained. This solution was extracted with ether and the aqueous solution was acidified to pH 1 with 3 N HCl. The mixture was cooled in an ice bath and N-(4-Toluenesulfonyl)imidazole-4-yl-acetic acid was isolated by filtration (white crystals, 1.10 g, 63% yield). m.p. 105-106° C. (decomp); 1H NMR (CDCl3) δ 10.0 (br, 1H), 8.04 (s, 1H), 7.82 (d, J=8.2 Hz, 2H), 7.37 (d, J=8.2 Hz, 2H), 7.28 (s, 1H), 3.65 (s, 2H), 2.45 (s, 3H). 13C NMR (CD3OD) δ 173.6, 148.1, 138.9, 138.0, 136.1, 131.6, 128.7, 117.0, 34.0, 21.6.

Workup

  1. customa clear solution was obtained
  2. extractionThis solution was extracted with ether
  3. temperatureThe mixture was cooled in an ice bath

Sources & evidence

ORD record
ord-a9f67ed878de489fa7f6e77743b81343
Source dataset
uspto-grants-2004_02
Patent number
US06693123B2

Reaction notes

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