p-Bromobenzenesulfonyl chloride → tert-Butyl {2-[(4-bromobenzene-1-sulfonyl)amino]ethyl}carbamate

HRID 1265217Notes

Reaction equation

HRID 1265217 reaction equation
[C:1]([O:5][C:6](=[O:11])[NH:7][CH2:8][CH2:9][NH2:10])([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.[Br:19][C:20]1[CH:25]=[CH:24][C:23]([S:26](Cl)(=[O:28])=[O:27])=[CH:22][CH:21]=1>C(Cl)Cl>[C:1]([O:5][C:6]([NH:7][CH2:8][CH2:9][NH:10][S:26]([C:23]1[CH:24]=[CH:25][C:20]([Br:19])=[CH:21][CH:22]=1)(=[O:28])=[O:27])=[O:11])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 7396p-Bromobenzenesulfonyl chlorideHCID 8471TriethylamineHCID 187201N-BOC-ethylenediamine

Product 1

HCID 7213233tert-Butyl {2-[(4-bromobenzene-1-sulfonyl)amino]ethyl}carbamateYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of N-(2-Aminoethyl)carbamic acid tert-butyl ester (1.86 g, 11.5 mmol) and triethyl amine (3 mL) in CH2Cl2 (100 mL) at 0° C., was added (4-bromophenyl)chlorosulfone (2.93 g, 11.5 mmol). The mixture was stirred for 3 hours, before the solvent was removed. The residue was dissolved in EtOAc (150 mL), washed with sat. NaHCO3 (50 mL), sat. NaCl (50 mL), 1N HCl (50 mL), sat. NaCl (2×50 mL), dried over MgSO4, and evaporated to give 3.8 g of the title compound as a white solid in 100% yield.

Workup

  1. customwas removed
  2. dissolutionThe residue was dissolved in EtOAc (150 mL)
  3. washwashed with sat. NaHCO3 (50 mL), sat. NaCl (50 mL), 1N HCl (50 mL), sat. NaCl (2×50 mL)
  4. dry with materialdried over MgSO4
  5. customevaporated

Sources & evidence

ORD record
ord-b0a44adad14946eeaa9c6a89781940b0
Source dataset
uspto-grants-2003_04
Patent number
US06545055B1

Reaction notes

Loading…