Dichloromethane → HCID 53839841, compound

HRID 1686989Notes

Reaction equation

[N+]([C:4]1[CH:5]=[C:6]2[C:12](=[CH:13][CH:14]=1)[CH:11]1[CH2:15][CH:7]2CN[CH2:10]1)([O-])=O.[CH2:16](N(CC)CC)[CH3:17].C(Cl)Cl.CS(Cl)(=O)=O.C(=O)(O)[O-].[Na+]>O>[CH3:16][CH:17]=[CH:5][CH:4]=[CH:14][CH:13]=[CH:12][CH2:6][CH2:7][CH2:15][CH2:11][CH3:10]

Participants

Conditions

Temperature: 0 °C

Procedure

In a 30 ml reaction vial 4-nitro-10-aza-tricyclo[6.3.1.0*2,7*]dodeca-2,4,6-triene (195 mg, 0.955 mmol), Triethylamine (0.40 mL, 2.9 mmol) were charged to methylene chloride (10 mL, 200 mmol). The reaction was cooled to 0° C. and the methanesulfonyl chloride (81 uL, 1.0 mmol) added dropwise with a syringe. The reaction was allowed to stir at 0° C. for 30 minutes. The reaction was poured into water (20 ml) and saturated sodium bicarbonate solution (20 ml) and the layers separated. The aqueous was washed with another 2×10 ml portions of methylene chloride. The combined organic was dried over magnesium sulfate, filtered and evaporated to yield 10-methanesulfonyl-4-nitro-10-aza tricycle[6.3.1.0*2,7*]dodeca-2,4,6-triene (170 mg, 63%) as a brown oil that was used crude in the next reaction. 1H-NMR (CDCl3) δ 8.17 (d, J=6.1 Hz, 1H), 8.13 (s, 1H), 7.39 (d, J=8.1 Hz, 1H), 3.77-3.68 (m, 2H), 3.41-3.28 (m, 4H), 2.52-2.42 (m, 1H), 2.30 (s, 3H), 1.92 (d, J=11.1 Hz), LC/MS (ESI+): 283 (M+H).

Workup

customthe layers separated
washThe aqueous was washed with another 2×10 ml portions of methylene chloride
dry with materialThe combined organic was dried over magnesium sulfate
filtrationfiltered
customevaporated

Sources & evidence

ORD record: ord-49d6df98570e41b284f3920f86ccb641
Source dataset: uspto-grants-2012_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08148391B2

Reaction notes

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