Dimethyl Sulfoxide → HCID 19023627, compound

HRID 1034170Notes

Reaction equation

HRID 1034170 reaction equation
[Cl:1][CH2:2][CH2:3][CH2:4][CH2:5][S:6]([C:9]1[CH:16]=[CH:15][CH:14]=[CH:13][C:10]=1[CH2:11][OH:12])(=[O:8])=[O:7].C(Cl)(=O)C(Cl)=O.CS(C)=O>C(N(CC)CC)C>[Cl:1][CH2:2][CH2:3][CH2:4][CH2:5][S:6]([C:9]1[CH:16]=[CH:15][CH:14]=[CH:13][C:10]=1[CH:11]=[O:12])(=[O:8])=[O:7]

Participants

5

Reactant 3

HCID 679Dimethyl SulfoxideHCID 65578Oxalyl chlorideHCID 53687522HCID 53687522, compound

Product 1

HCID 19023627HCID 19023627, compoundYield 88.2%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

2.8 g of 2-[(4-chlorobutyl)sulfonyl]benzyl alcohol was treated with 1.4 ml of oxalyl chloride, 2.4 ml of dimethylsulfoxide, and 7.8 ml of triethylamine in the same manner as described for Example 1, Part B. Purification of the crude product via column chromatography on silica gel, eluting with 60:10:30 toluene:ethyl acetate:hexane provided 2.45 g of the product. 1H-NMR (CDCl3) δ 1.91-1.97(m,4H); 3.35(t,2H,J=7 Hz); 3.54(t,2H,J=6 Hz); 7.80-7.85(m,2H); 8.07-8.14(m,2H); 10.75(s,1H). Mass spectrum: 261 (M+H).

Workup

  1. customPurification of the crude product via column chromatography on silica gel
  2. washeluting with 60:10:30 toluene

Sources & evidence

ORD record
ord-352c6e5b7b0740d48aa75d265ecdc679
Source dataset
uspto-grants-1994_05
Patent number
US05314887

Reaction notes

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