Ammonia → Tert-butyl 1-(4-chlorophenyl)-2-sulfamoylethylcarbamate

HRID 423091Notes

Reaction equation

HRID 423091 reaction equation
[NH3:1].[Cl:2][C:3]1[CH:8]=[CH:7][C:6]([CH:9]([NH:15][C:16](=[O:22])[O:17][C:18]([CH3:21])([CH3:20])[CH3:19])[CH2:10][S:11](Cl)(=[O:13])=[O:12])=[CH:5][CH:4]=1>C(#N)C>[Cl:2][C:3]1[CH:8]=[CH:7][C:6]([CH:9]([NH:15][C:16](=[O:22])[O:17][C:18]([CH3:21])([CH3:20])[CH3:19])[CH2:10][S:11](=[O:13])(=[O:12])[NH2:1])=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 222AmmoniaHCID 57750398Tert-butyl 1-(4-chlorophenyl)-2-(chlorosulfonyl)ethylcarbamate2×

Product 1

HCID 57750308Tert-butyl 1-(4-chlorophenyl)-2-sulfamoylethylcarbamateYield 68.5%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Ammonia (1.5 mL, 31.50 mmol) was added to a suspension of tert-butyl 1-(4-chlorophenyl)-2-(chlorosulfonyl)ethylcarbamate (Intermediate 78) (0.542 g, 1.53 mmol) in acetonitrile (10 mL). The mixture was stirred for 16 hours at room temperature. The mixture was partitioned between ethyl acetate and water and the organic layer was washed with brine. The organic solution was dried with magnesium sulfate, filtered, and concentrated under reduced pressure. The residue was purified by flash column chromatography on silica using gradient elution (10% ethyl acetate/DCM to 30% ethyl acetate/DCM). The desired product, tert-butyl 1-(4-chlorophenyl)-2-sulfamoylethylcarbamate (0.351 g, 68.5%), was thus isolated as a colourless solid.

Workup

  1. customThe mixture was partitioned between ethyl acetate and water
  2. washthe organic layer was washed with brine
  3. dry with materialThe organic solution was dried with magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by flash column chromatography on silica using gradient elution (10% ethyl acetate/DCM to 30% ethyl acetate/DCM)

Sources & evidence

ORD record
ord-d9db74a1e4bc4492b569bd6ae8323056
Source dataset
uspto-grants-2012_01
Patent number
US08101623B2

Reaction notes

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