Dimethylformamide → 4-(cyclopropylmethoxy)benzenesulfonyl Chloride

HRID 1591689Notes

Reaction equation

HRID 1591689 reaction equation
[Na+].[CH:2]1([CH2:5][O:6][C:7]2[CH:12]=[CH:11][C:10]([S:13]([O-:16])(=O)=[O:14])=[CH:9][CH:8]=2)[CH2:4][CH2:3]1.S(Cl)([Cl:19])=O.CN(C=O)C>>[CH:2]1([CH2:5][O:6][C:7]2[CH:12]=[CH:11][C:10]([S:13]([Cl:19])(=[O:16])=[O:14])=[CH:9][CH:8]=2)[CH2:4][CH2:3]1

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 24386Thionyl ChlorideHCID 236871614-Cyclopropylmethoxy-benzenesulfonic acid sodium salt

Product 1

HCID 113686084-(cyclopropylmethoxy)benzenesulfonyl Chloride

Procedure

To a suspention of 100 g (399.6 mmol) of 4-cyclopropylmethoxy-benzenesulfonic acid sodium salt, 186.55 ml (2557.5 mmol) of thionyl chloride and 6.19 ml (80 mmol) of DMF are added dropwise at r.t. After stirring for 15 h, the mixture is poured into ice water and extracted with CH2Cl2. The combined extracts are washed with H2O, dried over MgSO4 and concentrated under reduced pressure to give the title compound as a colorless solid; 1H-NMR (400 MHz, CDCl3): 0.35-0.45 (m, 2H), 0.65-0.75 (m, 2H), 1.25-1.35 (m, 1H), 3.91 (d, 2H, J=7.04 Hz), 7.02 (d, 2H, J=9.04 Hz), 7.96 (d, 2H, J=9.04 Hz).

Workup

  1. extractionextracted with CH2Cl2
  2. washThe combined extracts are washed with H2O
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-6660ac8d4c2841959aba6bb5edc96175
Source dataset
uspto-grants-2007_11
Patent number
US07291634B2

Reaction notes

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