Ethylene Glycol → HCID 11537368, compound

HRID 1984578Notes

Reaction equation

HRID 1984578 reaction equation
[CH2:1]([NH:3][S:4]([C:7]1[CH:12]=[CH:11][C:10](I)=[CH:9][CH:8]=1)(=[O:6])=[O:5])[CH3:2].C(O)CO.C(=O)([O-])[O-].[K+].[K+].[CH3:24][O:25][C:26]1[CH:33]=[CH:32][C:29]([CH2:30][SH:31])=[CH:28][CH:27]=1>C(O)(C)C.C(Cl)(Cl)Cl>[CH2:1]([NH:3][S:4]([C:7]1[CH:12]=[CH:11][C:10]([S:31][CH2:30][C:29]2[CH:32]=[CH:33][C:26]([O:25][CH3:24])=[CH:27][CH:28]=2)=[CH:9][CH:8]=1)(=[O:6])=[O:5])[CH3:2]

Participants

7

Reactant 4

HCID 174Ethylene GlycolHCID 11430Potassium CarbonateHCID 804074-Methoxy-alpha-toluenethiolHCID 2982277HCID 2982277, compound

Product 1

HCID 11537368HCID 11537368, compound

Reagents, catalysts & solvents 2

HCID 3776IsopropanolSolventHCID 6212ChloroformSolvent

Conditions

Temperature
80 °C

Procedure

To a suspension of N-ethyl-4-iodo-benzenesulfonamide 6 g in isopropanol 26 ml was added ethylene glycol 1.9 ml, potassium carbonate 4.68 g, cuprous iodide 320 mg and then 4-methoxybenzyl mercaptan 3.55 g. The mixture was heated at ˜80° C. for 16 h and then cooled, diluted with chloroform 250 ml and washed with water ×3, (any solid at the interface was filtered off). The organic solution was dried, MgSO4 and evaporated. The solid was triturated with cyclohexane ×2 and dried to give N-ethyl-4-(4-methoxy-benzylsulfanyl)-benzenesulfonamide, 5.98 g 92%. 1H NMR 7.63 (2H, d), 7.28 (2H, d), 7.18 (2H, d), 6.79 (2H, d), 4.40 (1H, m), 4.08 (1H, s), 3.72 (3H, s), 2.90 (2H, m), 1.03 (3H, t).

Workup

  1. temperaturecooled
  2. washwashed with water ×3
  3. filtration(any solid at the interface was filtered off)
  4. customThe organic solution was dried
  5. customMgSO4 and evaporated
  6. customThe solid was triturated with cyclohexane ×2
  7. customdried

Sources & evidence

ORD record
ord-d3cebffb24e84934aad4d7118ea45442
Source dataset
uspto-grants-2009_06
Patent number
US07544702B2

Reaction notes

Loading…