4-Methoxybenzenesulfonyl chloride → HCID 22997079, compound

HRID 29199Notes

Reaction equation

HRID 29199 reaction equation
[NH2:1][O:2][CH:3]([CH3:8])[CH2:4][CH2:5][C:6]#[N:7].[CH3:9][O:10][C:11]1[CH:16]=[CH:15][C:14](S(Cl)(=O)=O)=[CH:13][CH:12]=1.[CH:21](N(C(C)C)CC)(C)C.S(Cl)(Cl)(=O)=O.[OH-].[Na+]>C1COCC1.CN(C1C=CN=CC=1)C.C(OCC)C>[CH3:9][O:10][C:11]1[CH:16]=[CH:15][C:14]([CH2:21][NH:1][O:2][CH:3]([CH3:8])[CH2:4][CH2:5][C:6]#[N:7])=[CH:13][CH:12]=1

Participants

9

Reactant 5

HCID 74014-Methoxybenzenesulfonyl chlorideHCID 14798Sodium HydroxideHCID 24648Sulfuryl chlorideHCID 81531DiisopropylethylamineHCID 22997137HCID 22997137, compound

Product 1

HCID 22997079HCID 22997079, compoundYield 64%

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

4-(aminooxy)pentanenitrile (1.3 mmol, 150 mg) and 4-methoxybenzenesulfonylchloride (1.3 mmol, 272 mg) were combined in anhydrous THF with diisopropylethylamine (1.4 mmol, 0.69 mL) and a few crystals of DMAP. The reaction was stirred at 50° C. for 15 hours. The reaction was diluted in diethyl ether, washed with 1N HCl, 1N NaOH and brine and dried over mangesium sulfate. NMR analysis revealed that the isolated crude was the double sulfonyl chloride addition product. The aqueous NaOH fraction was acidified to neutral pH, extracted into ethyl acetate and dried over magnesium sulfate. The solvent was removed under vacuum leaving a very clean 195 mg (52%) crude product. Rf=0.4 (0.1:1 hexanes/ethyl acetate); H1-NMR (CDCl3): δ 7.82 (2H,d), 7.01 (2H,d), 6.84 (1H,s), 4.17 (1H,m), 3.88 (3H,s), 2.42 (2H,m), 1.88 (2H,m), 1.23 (3H,d).

Workup

  1. washwashed with 1N HCl, 1N NaOH and brine
  2. dry with materialdried over mangesium sulfate
  3. customisolated crude
  4. extractionextracted into ethyl acetate
  5. dry with materialdried over magnesium sulfate
  6. customThe solvent was removed under vacuum

Sources & evidence

ORD record
ord-ea1be3113c3e47f3ac9b0c63c220d977
Source dataset
uspto-grants-2008_09
Patent number
US07419967B2

Reaction notes

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