Acetic Anhydride → 5-Acetoxy-2-naphthalenesulfonyl chloride

HRID 725782Notes

Reaction equation

HRID 725782 reaction equation
[OH:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][C:6]([S:12]([OH:15])(=[O:14])=[O:13])=[CH:7]2.C(O[C:20](=[O:22])[CH3:21])(=O)C.[C:23]([O:26]S(O)(=O)=O)(=[O:25])[CH3:24].O=P(Cl)(Cl)[Cl:33].[N:36]1([CH:45]2[CH2:53][CH2:52][CH2:51][CH2:50][CH2:49][CH2:48]CC2)[CH2:44]CCCCCCC1>C(Cl)(Cl)Cl.N1C=CC=CC=1>[C:20]([O:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][C:6]([S:12]([N:36]1[CH2:44][CH:50]3[CH2:51][CH2:52][CH:53]([CH2:48][CH2:49]3)[CH2:45]1)(=[O:14])=[O:15])=[CH:7]2)(=[O:22])[CH3:21].[C:23]([O:26][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][C:6]([S:12]([Cl:33])(=[O:15])=[O:13])=[CH:7]2)(=[O:25])[CH3:24]

Participants

9

Reactant 5

HCID 7918Acetic AnhydrideHCID 24813Phosphorus oxychlorideHCID 3015046Acetyl sulfateHCID 30224535-Hydroxy-2-naphthalenesulfonic acidHCID 18706763HCID 18706763, compound

Product 2

HCID 197087075-Acetoxy-2-naphthalenesulfonyl chlorideHCID 197087183-(5-Acetoxy-2-naphthylsulfonyl)-3-azabicyclo[3.2.2]nonane

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6212ChloroformSolvent

Procedure

The title compound was prepared using a procedure similar to the procedure used to prepare Example 5. The 5-acetoxy-2-naphthalenesulfonyl chloride was prepared by acylating 0.30 g (1.25 mmol) of 5-hydroxy-2-naphthalenesulfonic acid with acetic anhydride and pyridine. The acetoxysulfonic acid was then treated with POCl3 yielding an orange oil, 0.26 g. The oil was reacted with 0.12 g (0.96 mmol) of the azabicyclononane in CHCl3 solution. The usual work-up gave 270 mg of a green oil. Purification by chromatotron using 8/1/1 hexane/acetone/chloroform gave a yellow oil, 75 mg (22% yield): 1H NMR (CDCl3): 8.34 (d, J=1.5, 1 H, H1), 7.99 (d, J=8.9, 1 H, H3), 7.87 (d, J=8.4, 1 H, H6), 7.78 (d, J=8.9, 1 H, H4), 7.60 (t, J=8.0, 1 H, H7), 7.40 (d, J=7.6, 1 H, H8), 3.29 (d, J=4.2, 4 H, N(CH2R)2), 2.50 (s, 3 H, CH3), 2.08 (s, 2 H, N(CH2CHR)2) 1.74-1.61 (m, 8 H, alkyl H's).

Workup

  1. customto prepare Example 5

Sources & evidence

ORD record
ord-b8b9aec8cf56407eb8e30ce95df6d8b4
Source dataset
uspto-grants-1998_01
Patent number
US05707985

Reaction notes

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