Water → HCID 86644416, compound

HRID 2194709Notes

Reaction equation

HRID 2194709 reaction equation
[OH:1][CH2:2][C:3]1[CH:7]=[C:6]([NH:8][C:9](=[O:16])[C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[N:5]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[N:4]=1.C(N(CC)CC)C.O>CS(C)=O>[CH:2]([C:3]1[CH:7]=[C:6]([NH:8][C:9](=[O:16])[C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[N:5]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[N:4]=1)=[O:1]

Participants

5

Reactant 3

HCID 962WaterHCID 8471TriethylamineHCID 68410469HCID 68410469, compound

Product 1

HCID 86644416HCID 86644416, compoundYield 79.5%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

N-[3-(Hydroxymethyl)-1-phenyl-1H-pyrazol-5-yl]benzamide (384 mg) and triethylamine (2 mL) were dissolved in dimethyl sulfoxide (5 mL), and sulfur trioxide•pyridine complex (417 mg) was added at room temperature. After stirring at room temperature for 18 hr, sulfur trioxide•pyridine complex (417 mg) was further added at room temperature and the mixture was stirred for 2 hr. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was washed with 2-propanol to give the title compound as a pale-yellow powder (yield 303 mg, yield 79%).

Workup

  1. additionsulfur trioxide•pyridine complex (417 mg) was added at room temperature
  2. additionsulfur trioxide•pyridine complex (417 mg) was further added at room temperature
  3. stirringthe mixture was stirred for 2 hr
  4. extractionthe mixture was extracted with ethyl acetate
  5. washThe extract was washed with saturated brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationconcentrated under reduced pressure
  8. washThe residue was washed with 2-propanol

Sources & evidence

ORD record
ord-3a0a8f94d0c344e48c33c192c6d1fea4
Source dataset
uspto-grants-2012_12
Patent number
US08334301B2

Reaction notes

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