Cesium carbonate → 1-Iodo-4-[4'-(1,1-dioxothiomorpholino)phenoxy] butane

HRID 369562Notes

Reaction equation

HRID 369562 reaction equation
[O:1]=[S:2]1(=[O:15])[CH2:7][CH2:6][N:5]([C:8]2[CH:13]=[CH:12][C:11]([OH:14])=[CH:10][CH:9]=2)[CH2:4][CH2:3]1.[I:16][CH2:17][CH2:18][CH2:19][CH2:20]I.C(=O)([O-])[O-].[Cs+].[Cs+]>C(#N)C>[I:16][CH2:17][CH2:18][CH2:19][CH2:20][O:14][C:11]1[CH:10]=[CH:9][C:8]([N:5]2[CH2:4][CH2:3][S:2](=[O:1])(=[O:15])[CH2:7][CH2:6]2)=[CH:13][CH:12]=1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 123371,4-DiiodobutaneHCID 218452234-(4-Hydroxyphenyl)thiomorpholine 1,1-Dioxide

Product 1

HCID 232822801-Iodo-4-[4'-(1,1-dioxothiomorpholino)phenoxy] butane

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 4-(1',1'-dioxothiomorpholino)phenol (10 g, 44 mmol), 1,4-diiodobutane (40.9 g, 132 mmol) and cesium carbonate (42.9 g, 132 mmol) was heated at 50° C. in acetonitrile (400 ml). After 4 hours, the reaction mixture was cooled, filtered and the solid salts washed with acetonitrile. The filtrate was poured into dilute HCl/ice water (1.2 l) and the resultant cream colored solid was isolated by filtration and washed with water. Chromatography on silica gel, with 97:3; dichloromethane:ether, afforded 1-iodo-4-[4'-(1,1-dioxothiomorpholino)phenoxy] butane, II (13.4 g, 74%). Mp. 119-121° C.

Workup

  1. temperaturethe reaction mixture was cooled
  2. filtrationfiltered
  3. washthe solid salts washed with acetonitrile
  4. additionThe filtrate was poured into dilute HCl/ice water (1.2 l)
  5. customthe resultant cream colored solid was isolated by filtration
  6. washwashed with water

Sources & evidence

ORD record
ord-a7e1f9f5241e4c1ba0e41ada628eaba2
Source dataset
uspto-grants-2000_10
Patent number
US06140031

Reaction notes

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