Hydrochloric Acid → Phenyl 3-(methanesulfonylaminocarbonyl)phenylcarbamate

HRID 1604595Notes

Reaction equation

HRID 1604595 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:12]=[CH:13][CH:14]=1)[C:5]([NH:7][S:8]([CH3:11])(=[O:10])=[O:9])=[O:6].Cl[C:16]([O:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)=[O:17].O.Cl>O1CCOCC1.[OH-].[Na+]>[CH3:11][S:8]([NH:7][C:5]([C:4]1[CH:3]=[C:2]([NH:1][C:16](=[O:17])[O:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH:14]=[CH:13][CH:12]=1)=[O:6])(=[O:10])=[O:9]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 15891Phenyl chloroformateHCID 212017011-(Methylsulphonylaminocarbonyl)-3-aminobenzene

Product 1

HCID 19603274Phenyl 3-(methanesulfonylaminocarbonyl)phenylcarbamateYield 96.1%

Reagents, catalysts & solvents 2

HCID 14798Sodium HydroxideSolventHCID 312751,4-DioxaneSolvent

Procedure

To a solution of N-(3-aminobenzoyl)methanesulfonamide (400 mg) in dioxane (4 ml) and 1N sodium hydroxide solution (3.73 ml) was added phenyl chloroformate (351 mg) under ice-cooling, and the mixture was stirred for 2.5 hours at ambient temperature. Water was added thereto, the mixture was adjusted pH 3 with hydrochloric acid. The mixture was extracted with chloroform-methanol, and the extract was dried over magnesium sulfate and concentrated in vacuo to give phenyl 3-(methanesulfonylaminocarbonyl)phenylcarbamate (600 mg) as colorless crystals.

Workup

  1. temperaturecooling
  2. extractionThe mixture was extracted with chloroform-methanol
  3. dry with materialthe extract was dried over magnesium sulfate
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-cab1cadfffd24f84880b46d3783ff733
Source dataset
uspto-grants-1999_11
Patent number
US05994368

Reaction notes

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