Potassium Nitrate → 1-(chloromethyl)-5-nitro-3-(trifluoroacetyl)-1,2-dihydro-3H-benzo[e]indole-7-sulfonyl chloride

HRID 2238372Notes

Reaction equation

HRID 2238372 reaction equation
[Cl:1][CH2:2][CH:3]1[C:11]2[C:10]3[CH:12]=[CH:13][C:14]([S:16]([Cl:19])(=[O:18])=[O:17])=[CH:15][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][C:14]([S:16]([Cl:19])(=[O:18])=[O:17])=[CH:15][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 445492671-(chloromethyl)-3-(trifluoroacetyl)-1,2-dihydro-3H-benzo[e]indole-7-sulfonyl chloride

Product 1

HCID 866202591-(chloromethyl)-5-nitro-3-(trifluoroacetyl)-1,2-dihydro-3H-benzo[e]indole-7-sulfonyl chlorideYield 67%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent2×

Procedure

A solution of 113(250 mg, 0.63 mmol) in conc. H2SO4 (10 mL) was nitrated with KNO3 (65 mg, 0.65 mmol) in H2SO4 (5 mL) as above, to give 1-(chloromethyl)-5-nitro-3-(trifluoroacetyl)-1,2-dihydro-3H-benzo[e]indole-7-sulfonyl chloride (116) (192 mg, 67%) as a red solid: mp (EtOAc/petroleum ether) 184-189° C.; 1H NMR [(CDCl3)] a 9.34 (s, 1H), 9.28 (d, J=1.8 Hz, 1H), 8.22 (dd, J=9.0, 1.9 Hz, 1H), 8.11 (d, J=9.0 Hz, 1H), 4.77-4.71 (m, 1H), 4.58 (dd, J=11.5, 8.8 Hz, 1H), 4.42-4.33 (m, 1H), 3.95 (dd, J=11.7, 3.5 Hz, 1H 3.73 (dd, J=11.7, 7.7 Hz, 1H); 13C NMR δ 153.4 (q, JC-F 38 Hz), 153.0, 148.2, 147.0, 138.7, 133.2, 129.1, 126.7, 124.5, 122.0, 119.3, 115.9 (q, JC-F 288 Hz), 52.6, 47.3, 41.2. Anal. (C15H9Cl2F3N2O5S) C, H, N, Cl.

Sources & evidence

ORD record
ord-5807e0b31bb74db3a9449a02819cfbfd
Source dataset
uspto-grants-2010_05
Patent number
US07718688B2

Reaction notes

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