Tetrahydrofuran → HCID 59353041, compound

HRID 1914717Notes

Reaction equation

HRID 1914717 reaction equation
Cl[CH2:2][C:3]1[N:4]([CH3:12])[CH:5]=[C:6]([S:8]([NH2:11])(=[O:10])=[O:9])[N:7]=1.C(=O)([O-])[O-:14].[K+].[K+].C1COCC1>O>[OH:14][CH2:2][C:3]1[N:4]([CH3:12])[CH:5]=[C:6]([S:8]([NH2:11])(=[O:10])=[O:9])[N:7]=1

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 11430Potassium CarbonateHCID 59352992HCID 59352992, compound

Product 1

HCID 59353041HCID 59353041, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a stirred suspension of 2-(chloromethyl)-1-methyl-1H-imidazole-4-sulfonamide (300 mg; 1.4 mmol; 1 eq) in water (5 mL) is added potassium carbonate (300 mg; 2.2 mmol; 1.5 eq) in portions and the reaction mixture is stirred at room temperature for 2 h. THF (5 mL) is added and reaction mixture is heated up to 60° C. for 3 h. The reaction mixture is cooled down and the THF is removed under reduced pressure. The resulting suspension is freeze dried to give 320 mg (contaminated with potassium salts) of the title compound as a white solid. 1H NMR (DMSO-d6) δ 7.58 (s, 1H), 7.10-6.40 (m, 2H), 4.18 (s, 2H), 3.68 (s, 3H). HPLC (max plot) 68%; Rt 0.96 min. LC/MS (ES+) 191.8; (ES−) 189.9.

Workup

  1. customreaction mixture
  2. temperatureis heated up to 60° C. for 3 h
  3. temperatureThe reaction mixture is cooled down
  4. customthe THF is removed under reduced pressure
  5. customdried

Sources & evidence

ORD record
ord-9a04080b1d144645b1f7248386e7b30c
Source dataset
uspto-grants-2013_12
Patent number
US08614215B2

Reaction notes

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