4-Toluenesulfonyl chloride → HCID 23436211, compound

HRID 2121156Notes

Reaction equation

HRID 2121156 reaction equation
[OH:1][CH2:2][C:3]1[N:4]=[C:5]([CH3:8])[NH:6][CH:7]=1.[C:9]1([CH3:19])[CH:14]=[CH:13][C:12]([S:15](Cl)(=[O:17])=[O:16])=[CH:11][CH:10]=1.[OH-].[Na+]>O.C1COCC1>[OH:1][CH2:2][C:3]1[N:4]=[C:5]([CH3:8])[N:6]([S:15]([C:12]2[CH:13]=[CH:14][C:9]([CH3:19])=[CH:10][CH:11]=2)(=[O:17])=[O:16])[CH:7]=1

Participants

6

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 14798Sodium HydroxideHCID 178432982HCID 178432982, compound

Product 1

HCID 23436211HCID 23436211, compoundYield 35%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

4-Hydroxymethyl-2-methylimidazole (0.7 g, 6.25 mmol), prepared as in Example 180A, and p-toluenesulfonylchloride (1.2 g, 6.25 mmol) were suspended in 5 mL of distilled water and 3 mL of THF. Sodium hydroxide (1N) was added to maintain a pH of 9 over a period of 3 hours. The reaction mixture was extracted with ethyl acetate (3×50 mL). The extracts were combined, dried over magnesium sulfate, concentrated and crystallized from ethyl acetate, collected by vacuum filtration and dried to give 4-hydroxymethyl-2-methyl-1-p-toluenesulfonylimidazole (0.5 g, 35%) as a white solid; m.p. 140-143°; 1H NMR (300 MHz, CDCl3) δ 7.78 (d, 8.25 2H), 7.36 (d, J=8.25 Hz, 2H), 7.33 (s, 1H), 4.49 (s, 2H), 2.50 (s, 3H), 2.45 (s, 3H); 13C NMR (75 MHz, CDCl3) δ 146.38, 140.96, 134.85, 130.51, 127.57, 116.05, 57.37, 21.84, 15.02; MS m/e calc'd: 266.0725, found: 266.0714.

Workup

  1. temperatureto maintain a pH of 9 over a period of 3 hours
  2. extractionThe reaction mixture was extracted with ethyl acetate (3×50 mL)
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated
  5. customcrystallized from ethyl acetate
  6. filtrationcollected by vacuum filtration
  7. customdried

Sources & evidence

ORD record
ord-6e429359b0be41179a285083115f4607
Source dataset
uspto-grants-2004_02
Patent number
US06693123B2

Reaction notes

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