Triethylamine → 2-Methylsulfonylamino-4-morpholin-4-yl-benzoic acid

HRID 884451Notes

Reaction equation

HRID 884451 reaction equation
[NH2:1][C:2]1[CH:10]=[C:9]([N:11]2[CH2:16][CH2:15][O:14][CH2:13][CH2:12]2)[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].CN([Si](C)(C)C)C(=O)C(F)(F)F.[CH3:29][S:30](Cl)(=[O:32])=[O:31].C(N(CC)CC)C>C(Cl)Cl>[CH3:29][S:30]([NH:1][C:2]1[CH:10]=[C:9]([N:11]2[CH2:12][CH2:13][O:14][CH2:15][CH2:16]2)[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5])(=[O:32])=[O:31]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 32510N-methyl-N-(trimethylsilyl)trifluoroacetamideHCID 178082042-Amino-4-(morpholin-4-yl)benzoic acid

Product 1

HCID 588052022-Methylsulfonylamino-4-morpholin-4-yl-benzoic acid

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a suspension of 2-amino-4-morpholin-4-ylbenzoic acid (230 mg; 1.04 mmol) in CH2Cl2 (3 mL) was added N-methyl-N-(trimethylsilyl)trifluoroacetamide (0.4 mL; 2.1 mmol) via syringe at room temperature under a nitrogen atmosphere. The resulting mixture was heated to reflux for 10 minutes, then allowed to cool to room temperature. Methanesulfonyl chloride (1.2 eq.) and triethylamine (1.2 eq.) were added, and the resulting mixture allowed to stir for 2 hours. The reaction was diluted with CH2Cl2 (30 mL) and washed with water (2×10 mL) and brine, then dried (MgSO4), filtered, and concentrated in vacuo to provide the sulfonamide as a white solid (280 mg; 90%).

Workup

  1. temperatureThe resulting mixture was heated
  2. temperatureto reflux for 10 minutes
  3. washwashed with water (2×10 mL) and brine
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-3decffbd6e1b4b29ac3696896c9a025a
Source dataset
uspto-grants-2012_08
Patent number
US08242115B2

Reaction notes

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