Potassium Nitrate → HCID 87540981, compound

HRID 2238371Notes

Reaction equation

HRID 2238371 reaction equation
[Cl:1][CH2:2][CH:3]1[C:11]2[C:10]3[CH:12]=[CH:13][CH:14]=[C:15]([S:16]([Cl:19])(=[O:18])=[O:17])[C:9]=3[CH:8]=[CH:7][C:6]=2[N:5]([C:20](=[O:25])[C:21]([F:24])([F:23])[F:22])[CH2:4]1.[N+:26]([O-])([O-:28])=[O:27].[K+]>OS(O)(=O)=O>[Cl:1][CH2:2][CH:3]1[C:11]2[C:10]3[CH:12]=[CH:13][CH:14]=[C:15]([S:16]([Cl:19])(=[O:18])=[O:17])[C:9]=3[C:8]([N+:26]([O-:28])=[O:27])=[CH:7][C:6]=2[N:5]([C:20](=[O:25])[C:21]([F:24])([F:23])[F:22])[CH2:4]1

Participants

4

Reactant 2

HCID 24434Potassium NitrateHCID 44549268HCID 44549268, compound

Product 1

HCID 87540981HCID 87540981, compoundYield 59%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent2×

Procedure

The 6-sulfonyl chloride 114(750 mg, 1.9 mmol) was dissolved in conc. H2SO4 (20 mL), the solution was cooled in an ice bath, and a solution of KNO3 (195 mg, 1.95 mmol) in H2SO4 (5 mL) was added slowly. The mixture was vigorously for 30 min, quenched with cold water, and extracted with EtOAc (3×50 mL). The extracts were dried and concentrated under reduced pressure, and the resulting solid was separated by column chromatography on silica gel. Elution with EtOAc/petroleum ether (from 1:4 to 1:1) gave 1-(chloromethyl)-5-nitro-3-(trifluoroacetyl)-1,2-dihydro-3H-benzo[e]indole-6-sulfonyl chloride (115) (202 mg, 59%, based on consumption of starting material): mp (EtOAc/petroleum ether) 169° C. (dec.); 1H NMR [(CD3)2SO] δ 8.63 (s, 1H), 8.22 (dd, J=7.6, 0.9 Hz, 1H), 8.13 (dd, J=8.4 Hz, 1H), 7.71 (dd, J=7.8, 7.8 Hz, 1H), 4.66-4.56 (m, 2H), 4.49-4.43 (m, 1H), 4.17-4.02 (m, 2H); 13C NMR δ 153.4 (q, JC-F 37.4 Hz), 149.2, 145.2, 137.7, 131.4, 130.5, 129.9, 127.7, 124.9, 118.6, 115.6 (q, JC-F 288 Hz) 114.3, 52.6, 47.5, 41.4. Anal. (C15H9Cl2F3N2O5S) C, H, N. 114 (457 mg, 61%) was also recovered.

Workup

  1. temperaturethe solution was cooled in an ice bath
  2. customquenched with cold water
  3. extractionextracted with EtOAc (3×50 mL)
  4. customThe extracts were dried
  5. concentrationconcentrated under reduced pressure
  6. customthe resulting solid was separated by column chromatography on silica gel
  7. washElution with EtOAc/petroleum ether (from 1:4 to 1:1)

Sources & evidence

ORD record
ord-a4d816dbad3740dfaea67cbb15724179
Source dataset
uspto-grants-2010_05
Patent number
US07718688B2

Reaction notes

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