Hydrochloric Acid → N-Cyclopropyl-5-(2,6-dichloro-4-nitro-phenoxy)-2-methoxy-benzenesulfonamide

HRID 432909Notes

Reaction equation

[Cl:1][C:2]1[CH:20]=[C:19]([N+:21]([O-:23])=[O:22])[CH:18]=[C:17]([Cl:24])[C:3]=1[O:4][C:5]1[CH:6]=[CH:7][C:8]([O:15][CH3:16])=[C:9]([S:11](Cl)(=[O:13])=[O:12])[CH:10]=1.C(N(CC)CC)C.[CH:32]1([NH2:35])[CH2:34][CH2:33]1.Cl>C(Cl)Cl.O>[CH:32]1([NH:35][S:11]([C:9]2[CH:10]=[C:5]([O:4][C:3]3[C:2]([Cl:1])=[CH:20][C:19]([N+:21]([O-:23])=[O:22])=[CH:18][C:17]=3[Cl:24])[CH:6]=[CH:7][C:8]=2[O:15][CH3:16])(=[O:13])=[O:12])[CH2:34][CH2:33]1

Participants

Conditions

Temperature: 0 °C

Procedure

To a cooled solution of 5-(2,6-dichloro-4-nitro-phenoxy)-2-methoxy-benzenesulfonyl chloride (920 mg, 2.2 mmol) in CH2Cl2 (25 mL) at 0° C. was added triethylamine (470 μL, 3.4 mmol) and cyclopropylamine (170 μL, 2.5 mol). The resulting mixture was stirred at 0° C. for 5 min, then at RT for 6 h. Water (30 mL) and 1N HCl (1 mL) was added and the solution was extracted with EtOAc (3×50 mL). The combined EtOAc extracts were dried and concentrated. The product was purified by chromatography to give the title compound of Step B (652 mg). MS (APCl) Calc.: 432.0, Found: 430.9 (M−1).

Workup

waitat RT for 6 h
extractionthe solution was extracted with EtOAc (3×50 mL)
dry with materialThe combined EtOAc extracts were dried
concentrationconcentrated
customThe product was purified by chromatography

Sources & evidence

ORD record: ord-743a1107364c418a9b315b69b54a9955
Source dataset: uspto-grants-2003_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06664291B2

Reaction notes

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