Hydrochloric Acid → 4-[(Azetidin-3-ylmethyl)sulfonyl]benzonitrile Hydrochloride

HRID 10214Notes

Reaction equation

HRID 10214 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([S:9]([CH2:12][CH:13]2[CH2:16][N:15](C(OC(C)(C)C)=O)[CH2:14]2)(=[O:11])=[O:10])=[CH:5][CH:4]=1)#[N:2].[ClH:24]>O1CCOCC1>[ClH:24].[NH:15]1[CH2:16][CH:13]([CH2:12][S:9]([C:6]2[CH:7]=[CH:8][C:3]([C:1]#[N:2])=[CH:4][CH:5]=2)(=[O:11])=[O:10])[CH2:14]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 21978362HCID 21978362, compound

Product 1

HCID 219784144-[(Azetidin-3-ylmethyl)sulfonyl]benzonitrile Hydrochloride

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

The foregoing tert-butyl 3-{[(4-cyanophenyl)sulfonyl]methyl}azetidine-1-carboxylate (200 mg, 0.59 mmol) was treated with 4N HCl in 1,4-dioxane and stirred for 10 minutes. The reaction was evaporated without heat to give the title compound crude as a white solid (100 mg). 1H NMR (500 MHz, CDCl3) δ 2.99–3.05 (1H, m), 3.78 (2H, t, J=7.8 Hz), 3.86–3.94 (4H, m), 8.08 (2H, d, J=8.6 Hz), 8.20 (2H, d, J=8.6 Hz), 8.95 (2H, br s).

Workup

  1. customThe reaction was evaporated
  2. temperaturewithout heat

Sources & evidence

ORD record
ord-f59d6193c6e348fe991b92af4f65b3da
Source dataset
uspto-grants-2006_08
Patent number
US07094777B2

Reaction notes

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