Benzenesulfonyl chloride → HCID 20677518, compound

HRID 366147Notes

Reaction equation

HRID 366147 reaction equation
[C:1]([O:5][C:6](=[O:18])[N:7]([CH2:9][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[NH2:17])[CH3:8])([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.[C:26]1([S:32](Cl)(=[O:34])=[O:33])[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1>ClCCl.C(OCC)(=O)C>[C:1]([O:5][C:6](=[O:18])[N:7]([CH2:9][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[NH:17][S:32]([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)(=[O:34])=[O:33])[CH3:8])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 3

HCID 7369Benzenesulfonyl chlorideHCID 8471TriethylamineHCID 10800697N-(2-(2-aminophenyl)ethyl)-N-methylcarbamic acid tert-butyl ester

Product 1

HCID 20677518HCID 20677518, compoundYield 64.3%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
-78 °C

Procedure

N-(2-(2-Aminophenyl)ethyl)-N-methylcarbamic acid tert-butyl ester (555 mg, 2.22 mmol) and triethylamine (0.40 ml, 2.66 mmol) were dissolved in dichloromethane (12 ml) and cooled to -78° C. A solution of benzenesulfonyl chloride (0.28 ml, 2.22 mmol) in dichloromethane (3 ml) was added dropwise. The solution was stirred for 16 h, while it was warming up to room temperature. It was diluted with ethyl acetate (40 ml) and washed with 10% aqueous sodium hydrogen sulfate solution (20 ml). The aqueous phase was extracted with ethyl acetate (2×15 ml). The combined organic layers were washed with saturated aqueous sodium hydrogen carbonate solution (30 ml) and dried over magnesium sulfate. The solvent was removed in vacuo. The crude product was purified by flash chromatography on silica (30 g), using ethyl acetate/heptane 1:3 as eluent, to give 557 mg of N-[2-(2-(phenylsulfonylamino)phenyl)ethyl]-N-methylcarbamic acid tert-butyl ester.

Workup

  1. temperaturewas warming up to room temperature
  2. washwashed with 10% aqueous sodium hydrogen sulfate solution (20 ml)
  3. extractionThe aqueous phase was extracted with ethyl acetate (2×15 ml)
  4. washThe combined organic layers were washed with saturated aqueous sodium hydrogen carbonate solution (30 ml)
  5. dry with materialdried over magnesium sulfate
  6. customThe solvent was removed in vacuo
  7. customThe crude product was purified by flash chromatography on silica (30 g)

Sources & evidence

ORD record
ord-1e92116c502c44e0b67c1af6cbd7f3c8
Source dataset
uspto-grants-2000_10
Patent number
US06127354

Reaction notes

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