4-Iodobenzenesulfonyl chloride → 4-(4-Iodophenyl)sulfonylmorpholine

HRID 1726877Notes

Reaction equation

HRID 1726877 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.C(N(CC)CC)C.[NH:19]1[CH2:24][CH2:23][O:22][CH2:21][CH2:20]1.C(OC(C)C)(C)C>C(Cl)Cl>[I:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([N:19]2[CH2:24][CH2:23][O:22][CH2:21][CH2:20]2)(=[O:10])=[O:9])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 73994-Iodobenzenesulfonyl chlorideHCID 7914Diisopropyl EtherHCID 8083MorpholineHCID 8471Triethylamine

Product 1

HCID 38002234-(4-Iodophenyl)sulfonylmorpholine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 50 g of 4-iodobenzenesulphonyl chloride (0.165 mol) in 500 ml of CH2Cl2 there are added 46 ml of triethylamine (0.33 mol) and then, dropwise, 17 ml of morpholine (0.198 mol). Because the reaction is exothermic, the flask is placed in an ice bath until it has returned to ambient temperature. The reaction mixture is stirred for 1 hour at ambient temperature. After washing the reaction mixture with about 100 ml of 1N HCl and then 100 ml of water, the organic phase is dried (MgSO4) and evaporated under reduced pressure. The solid residue thereby obtained is re-suspended in a small amount of isopropyl ether to yield the title product after filtration and drying in vacuo.

Workup

  1. customthe flask is placed in an ice bath until it
  2. customhas returned to ambient temperature
  3. washAfter washing the reaction mixture with about 100 ml of 1N HCl
  4. dry with material100 ml of water, the organic phase is dried (MgSO4)
  5. customevaporated under reduced pressure
  6. customThe solid residue thereby obtained

Sources & evidence

ORD record
ord-e47ddc4d52b84fc5902562ac3590e39e
Source dataset
uspto-grants-2009_02
Patent number
US07494994B2

Reaction notes

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