Ammonium Chloride → HCID 47269479, compound

HRID 1820224Notes

Reaction equation

HRID 1820224 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:6]=[C:7]([CH:11]=[CH:12][CH:13]=1)[C:8](O)=[O:9])=[O:4].[CH3:14][S:15]([NH2:18])(=[O:17])=[O:16].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N(C(C)C)CC)(C)C.[Cl-].[NH4+]>C(Cl)Cl>[CH3:14][S:15]([NH:18][C:8]([C:7]1[CH:6]=[C:5]([CH:13]=[CH:12][CH:11]=1)[C:3]([O:2][CH3:1])=[O:4])=[O:9])(=[O:17])=[O:16]

Participants

7

Reactant 5

HCID 25517Ammonium ChlorideHCID 72879MethanesulfonamideHCID 81531DiisopropylethylamineHCID 6018803-(Methoxycarbonyl)benzoic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

Product 1

HCID 47269479HCID 47269479, compoundYield 97.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3-(Methoxycarbonyl)benzoic acid (500 mg, 2.78 mmol), methyl sulfonamide (264 mg, 2.78 mmol), HATU (1.06 g, 2.78 mmol), and diisopropylethylamine (1.45 mL, 8.33 mmol) were mixed in methylene chloride (20 mL) with stirring. The reaction was stirred for 20 hours, added sat'd ammonium chloride, and extracted with methylene chloride. The organic extracts were combined, dried over sodium sulfate and concentrated to give an amber oil which was purified over silica gel (1:1 hexanes/ethyl acetate to 100% ethyl acetate to 4:1 methylene chloride/methanol) to obtain methyl 3-(methylsulfonylcarbamoyl)benzoate (700 mg, 2.72 mmol, 97% yield). MS found: (M+H)+=258.07.

Workup

  1. stirringThe reaction was stirred for 20 hours
  2. extractionextracted with methylene chloride
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated
  5. customto give an amber oil which
  6. customwas purified over silica gel (1:1 hexanes/ethyl acetate to 100% ethyl acetate to 4:1 methylene chloride/methanol)

Sources & evidence

ORD record
ord-5179dfc6fedf4878b950dd975bb3eed2
Source dataset
uspto-grants-2009_10
Patent number
US07601844B2

Reaction notes

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