4-Iodobenzenesulfonyl chloride → HCID 1587718, compound

HRID 1064333Notes

Reaction equation

HRID 1064333 reaction equation
[I:1][C:2]1[CH:7]=[CH:6][C:5]([S:8](Cl)(=[O:10])=[O:9])=[CH:4][CH:3]=1.[CH3:12][O:13][CH2:14][CH2:15][NH2:16].C(N(CC)CC)C>C(Cl)Cl>[CH3:12][O:13][CH2:14][CH2:15][NH:16][S:8]([C:5]1[CH:6]=[CH:7][C:2]([I:1])=[CH:3][CH:4]=1)(=[O:10])=[O:9]

Participants

5

Reactant 3

HCID 73994-Iodobenzenesulfonyl chlorideHCID 80182-MethoxyethylamineHCID 8471Triethylamine

Product 1

HCID 1587718HCID 1587718, compoundYield 100.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

A solution of 4-iodophenylsulphonyl chloride (3.64 g, 12 mmol) in DCM (30 ml) was added dropwise to a solution of 2-methoxyethylamine (1.3 ml, 15 mmol) and triethylamine (2 ml, 15 mmol) in DCM (60 ml) cooled by an ice bath to 0° C. The mixture was then allowed to warm to ambient temperature and stirred for 1 hour. The solvent was removed by evaporation and the resulting oil dissolved EtOAc (100 ml) and washed with 1N aqueous citric acid solution (2×100 ml), brine (100 ml) and dried. The volatiles were removed by evaporation to give the title compound (4.1 g, 100%) as a clear oil. NMR 3.12 (2H, q), 3.28 (3H, s), 3.44 (2H, t), 4.90 (1H, t), 7.57 (2H, d), 7.81 (2H, d); m/z: 342.

Workup

  1. temperatureto warm to ambient temperature
  2. customThe solvent was removed by evaporation
  3. dissolutionthe resulting oil dissolved EtOAc (100 ml)
  4. washwashed with 1N aqueous citric acid solution (2×100 ml), brine (100 ml)
  5. customdried
  6. customThe volatiles were removed by evaporation

Sources & evidence

ORD record
ord-5478d448dcb24a6dbb98f4b86355f360
Source dataset
uspto-grants-2005_11
Patent number
US06969714B2

Reaction notes

Loading…