4-Iodobenzenesulfonyl chloride → N-(2-ethoxyethyl)-4-iodobenzenesulphonamide

HRID 2375281Notes

Reaction equation

HRID 2375281 reaction equation
[CH2:1]([O:3][CH2:4][CH2:5][NH2:6])[CH3:2].C(N(C(C)C)CC)(C)C.[CH:16]1[C:21]([S:22](Cl)(=[O:24])=[O:23])=[CH:20][CH:19]=[C:18]([I:26])[CH:17]=1>C(Cl)Cl>[CH2:1]([O:3][CH2:4][CH2:5][NH:6][S:22]([C:21]1[CH:16]=[CH:17][C:18]([I:26])=[CH:19][CH:20]=1)(=[O:24])=[O:23])[CH3:2]

Participants

5

Reactant 3

HCID 73994-Iodobenzenesulfonyl chlorideHCID 66970EthoxyethylamineHCID 81531Diisopropylethylamine

Product 1

HCID 3870475N-(2-ethoxyethyl)-4-iodobenzenesulphonamideYield 98.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

2-Ethoxyethylamine (2.14 g, 24 mmol) and diisopropylethylamine (4.2 ml, 24 mmol) were dissolved in DCM (50 ml) and cooled to 0° C. To this was added pipsyl chloride (6.05 g, 20 mmol) in portions and the reaction stirred for 18 hours. Volatiles were evaporated in vacuo. The residue was dissolved in EtOAc (50 ml), washed with 0.33M citric acid (2×50 ml), brine (50 ml), dried and evaporated in vacuo to yield an oil which solidified on standing to give the title compound as a pale yellow solid (6.97 g, 98%). NMR: 1.01 (t, 3H), 2.89 (q, 2H), 3.30 (m, 4H), 7.53 (d, 2H), 7.75 (t, 1H), 7.97 (d, 2H); m/z 354 (M−H)−.

Workup

  1. customVolatiles were evaporated in vacuo
  2. dissolutionThe residue was dissolved in EtOAc (50 ml)
  3. washwashed with 0.33M citric acid (2×50 ml), brine (50 ml)
  4. customdried
  5. customevaporated in vacuo
  6. customto yield an oil which

Sources & evidence

ORD record
ord-101bce8bac0e4773a00bb82ec7db40c6
Source dataset
uspto-grants-2008_12
Patent number
US07465728B2

Reaction notes

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