Potassium Nitrate → HCID 86620263, compound

HRID 2238442Notes

Reaction equation

HRID 2238442 reaction equation
[Cl:1][CH2:2][CH:3]1[C:11]2[C:10]3[CH:12]=[C:13]([S:19]([NH2:22])(=[O:21])=[O:20])[C:14]([N+:16]([O-:18])=[O:17])=[CH:15][C:9]=3[CH:8]=[CH:7][C:6]=2[N:5]([C:23](=[O:28])[C:24]([F:27])([F:26])[F:25])[CH2:4]1.[N+:29]([O-])([O-:31])=[O:30].[K+]>OS(O)(=O)=O>[Cl:1][CH2:2][CH:3]1[C:11]2[C:10]3[CH:12]=[C:13]([S:19]([NH2:22])(=[O:21])=[O:20])[C:14]([N+:16]([O-:18])=[O:17])=[CH:15][C:9]=3[C:8]([N+:29]([O-:31])=[O:30])=[CH:7][C:6]=2[N:5]([C:23](=[O:28])[C:24]([F:27])([F:26])[F:25])[CH2:4]1

Participants

4

Reactant 2

HCID 24434Potassium NitrateHCID 86620264HCID 86620264, compound

Product 1

HCID 86620263HCID 86620263, compoundYield 21%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

Ice cold H2SO4 (98%, 5 mL) was added to 218 (30 mg, 0.069 mmol) at 0° C. with stirring. An ice-cold solution of KNO3 (9 mg, 0.089 mmol) in H2SO4 (98%, 1 mL) was then added dropwise. After 1 h the mixture was poured into ice water and extracted with EtOAc (×3). The combined EtOAc extracts were washed with H2O, brine and dried. Chromatography eluting with petroleum ether/EtOAc (1:1) gave 1-(chloromethyl)-5,7-dinitro-3-(trifluoroacetyl)-1,2-dihydro-3H-benzo[e]indole-8-sulfonamide (219) (7 mg, 21%) as an orange powder: mp 201-204° C.; 1H NMR (CDCl3) δ 9.49 (s, 1H), 9.29 (s, 1H), 8.71 (s, 1H), 5.67 (s, 2H), 4.73 (d, J=10.8 Hz, 1H), 4.62 (dd, J=11.3, 8.8 Hz, 1H), 4.52-4.45 (m, 1H), 3.97 (dd, J=11.8, 3.5 Hz, 1H), 3.85 (dd, J=11.8, 6.3 Hz, 1H). HRMS (FAB) calcd. for C15H1135ClF3N4O7S (MH+) m/z 482.9989, found 482.9988.

Workup

  1. extractionextracted with EtOAc (×3)
  2. washThe combined EtOAc extracts were washed with H2O, brine
  3. customdried
  4. washChromatography eluting with petroleum ether/EtOAc (1:1)

Sources & evidence

ORD record
ord-80892b7ee8a244d588a90bf1aaff1f79
Source dataset
uspto-grants-2010_05
Patent number
US07718688B2

Reaction notes

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