Diethylamine → 3-(Diethylsulfamoyl)benzoic acid

HRID 713801

Reaction equation

[CH2:1]([NH:3][CH2:4][CH3:5])[CH3:2].Cl[S:7]([C:10]1[CH:11]=[C:12]([CH:16]=[CH:17][CH:18]=1)[C:13]([OH:15])=[O:14])(=[O:9])=[O:8]>ClCCl>[CH2:1]([N:3]([CH2:4][CH3:5])[S:7]([C:10]1[CH:11]=[C:12]([CH:16]=[CH:17][CH:18]=1)[C:13]([OH:15])=[O:14])(=[O:9])=[O:8])[CH3:2]

Participants

Conditions

Temperature: 0 °C

Procedure

Diethylamine (Aldrich, 2.5 mL, 24 mmol) was added to a solution of 3-(chlorosulfonyl)benzoic acid (Aldrich, 2.0 g, 9.1 mmol) in anhydrous dichloromethane (20 mL) at 0° C. The mixture was then stirred at 0° C. for 2 hours. The volatiles were removed under reduced pressure. The residue was treated with aqueous potassium hydrogensulfate (1 M, 10 mL) and then extracted with ethyl acetate (3×50 mL). The combined extracts were dried over magnesium sulfate filtered and then concentrated to give the title compound. 1H NMR (300 MHz, CD3OD) δ 1.13 (t, J=7.1 Hz, 6H), 3.22-3.30 (m, 4H), 7.69 (t, J=7.8 Hz, 1H), 8.03 (ddd, J=7.9, 1.9, 1.4 Hz, 1H), 8.25 (dt, J=7.8, 1.4 Hz, 1H), 8.40 (t, J=1.7 Hz, 1H) ppm; MS (DCl/NH3) m/z 275 (M+NH4)+.

Workup

customThe volatiles were removed under reduced pressure
additionThe residue was treated with aqueous potassium hydrogensulfate (1 M, 10 mL)
extractionextracted with ethyl acetate (3×50 mL)
dry with materialThe combined extracts were dried over magnesium sulfate
filtrationfiltered
concentrationconcentrated

Sources & evidence

ORD record: ord-539e8e4deba14203bded6843cd708a21
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09186407B2

Linked notes

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