Tetrahydrofuran → HCID 178491755, compound

HRID 1517385Notes

Reaction equation

HRID 1517385 reaction equation
S(Cl)([Cl:3])=O.O[CH2:6][C:7]1[C:12]2[NH:13][C:14]([CH2:16][N:17]([CH3:31])[S:18]([C:21]3[C:26]([CH3:27])=[CH:25][C:24]([O:28][CH3:29])=[CH:23][C:22]=3[CH3:30])(=[O:20])=[O:19])=[N:15][C:11]=2[CH:10]=[CH:9][CH:8]=1.C1COCC1>C(OCC)(=O)C>[Cl:3][CH2:6][C:7]1[C:12]2[NH:13][C:14]([CH2:16][N:17]([CH3:31])[S:18]([C:21]3[C:26]([CH3:27])=[CH:25][C:24]([O:28][CH3:29])=[CH:23][C:22]=3[CH3:30])(=[O:20])=[O:19])=[N:15][C:11]=2[CH:10]=[CH:9][CH:8]=1

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 24386Thionyl ChlorideHCID 178491757HCID 178491757, compound

Product 1

HCID 178491755HCID 178491755, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Thionyl chloride (3.22 mmol, 2.5 eq.) was added to a cooled (0° C.) solution of N-((7-(hydroxymethyl)-1H-benzo[d]imidazol-2-yl)methyl)-4-methoxy-N,2,6-trimethylbenzenesulfonamide (1.29 mmol, 1.0 eq.) in abs. THF (10 ml). The reaction mixture was stirred at room temperature for 24 h. The mixture was then diluted with ethyl acetate and washed successively with NaHCO3 solution and NaCl solution. The organic phase was dried over Na2SO4 and the solvent was distilled off in vacuo to obtain the crude product, which led to the desired product by purification by column chromatography over silica gel. Yield: 76%

Workup

  1. washwashed successively with NaHCO3 solution and NaCl solution
  2. dry with materialThe organic phase was dried over Na2SO4
  3. distillationthe solvent was distilled off in vacuo

Sources & evidence

ORD record
ord-2f150754de9c47cfa1b54ab907a4b0ec
Source dataset
uspto-grants-2012_07
Patent number
US08232288B2

Reaction notes

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