1-(Chloromethyl)-3,5-bis(trifluoromethyl)benzene → HCID 86641705, Verbindung

HRID 602568

Reaktionsgleichung

Reaktionsgleichung von HRID 602568
[CH3:1][C:2]1[N:9]2[C:5](=[N:6][C:7]3[CH:13]=[CH:12][CH:11]=[CH:10][C:8]=32)[S:4][CH:3]=1.[F:14][C:15]([F:29])([F:28])[C:16]1[CH:17]=[C:18]([CH:21]=[C:22]([C:24]([F:27])([F:26])[F:25])[CH:23]=1)[CH2:19][Cl:20]>C(#N)C>[Cl-:20].[F:14][C:15]([F:28])([F:29])[C:16]1[CH:17]=[C:18]([CH:21]=[C:22]([C:24]([F:27])([F:25])[F:26])[CH:23]=1)[CH2:19][N+:6]1[C:7]2[CH:13]=[CH:12][CH:11]=[CH:10][C:8]=2[N:9]2[C:2]([CH3:1])=[CH:3][S:4][C:5]=12

Komponenten

4

Edukt 2

HCID 1235761-(Chloromethyl)-3,5-bis(trifluoromethyl)benzeneHCID 8282853-Methyl[1,3]thiazolo[3,2-a]benzimidazole

Produkt 1

HCID 86641705HCID 86641705, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

198 mg of 3-methyl[1,3]thiazolo[3,2-a]benzimidazole were solubilised in acetonitrile (2 mL). Then 828 mg (3 eq) of 3,5-bis(trifluoromethyl)benzyl chloride were added and the solution stirred under reflux. After 18 h, 9-[3,5-bis(trifluoromethyl)benzyl]-3-methyl[1,3]thiazolo[3,2-a]benzimidazol-9-ium chloride was recovered as a white powder (422 mg, 89%) by filtration. Mp>268° C.; 1H NMR (300 MHz, MeOD) δ=2.95 (3H, d, J=1.3, CH3), 6.03 (2H, s, CH2), 7.30 (1H, q, J=1.3, H5), 7.70-7.83 (2H, m, Ar), 8.02-8.04 (1H, m, Ar), 8.11 (1H, brs, Ar), 8.21 (2H, brs, Ar), 8.31-8.34 (1H, m, Ar); 13C NMR (75 MHz, MeOD) δ=14.11, 50.33, 112.73, 113.72, 115.13, 124.43 (1C, sept, J=4), 124.46 (2C, q, J=272), 126.67, 128.66, 129.20, 130.92 (2C, q, J=3), 133.72 (2C, q, J=34), 135.48, 136.62, 137.71, 156.38; HRMS m/z C19H13F6N2S [M−Cl]+ calcd: 415.0698, found: 415.0698.

Aufarbeitung

  1. temperatureunder reflux
  2. filtration9-[3,5-bis(trifluoromethyl)benzyl]-3-methyl[1,3]thiazolo[3,2-a]benzimidazol-9-ium chloride was recovered as a white powder (422 mg, 89%) by filtration

Quellen und Nachweise

ORD-Eintrag
ord-dc6db1d22ee14491be74b872f4b40744
Quelldatensatz
uspto-grants-2011_03
Patentnummer
US07906541B2

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