4-Iodobenzenesulfonyl chloride → HCID 1587718, compound

HRID 1723662Notes

Reaction equation

HRID 1723662 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 0.33 M 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 0.33 M aqueous citric acid solution (2×100 ml), brine (100 ml)
  5. customdried
  6. customThe volatiles were removed by evaporation

Sources & evidence

ORD record
ord-151cf938a0ce42ac9605a0f686c9ecea
Source dataset
uspto-grants-2009_02
Patent number
US07485638B2

Reaction notes

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