1-Iodoheptane → 9-Heptyl-3-methyl[1,3]thiazolo[3,2-a]benzimidazol-9-ium iodide

HRID 602570Notes

Reaction equation

HRID 602570 reaction equation
[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.[I:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21]>>[I-:14].[CH2:15]([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)[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21]

Participants

3

Reactant 2

HCID 202741-IodoheptaneHCID 8282853-Methyl[1,3]thiazolo[3,2-a]benzimidazole

Product 1

HCID 866417069-Heptyl-3-methyl[1,3]thiazolo[3,2-a]benzimidazol-9-ium iodide

Procedure

198 mg of 3-methyl[1,3]thiazolo[3,2-a]benzimidazole were added to 1-iodoheptane (3 mL). Then the mixture was stirred under reflux. After 18 h, 9-heptyl-3-methyl[1,3]thiazolo[3,2-a]benzimidazol-9-ium iodide was recovered as a pale green powder (421 mg, 97%) by filtration. Mp 137° C.; 1H NMR (300 MHz, MeOD) δ=0.8-0.91 (3H, m, CH3), 1.22-1.54 (8H, m, 4-CH2), 2.05 (2H, quint, J=7.4, CH2), 2.95 (3H, d, J=1.3, CH3), 4.60 (2H, t, J=7.2, CH2), 7.36 (1H, q, J=1.3, H5), 7.64-7.82 (2H, m, Ar), 7.99-8.05 (1H, m, Ar), 8.26-8.32 (1H, m, Ar); 13C NMR (75 MHz, MeOD) δ=14.26, 14.35, 23.57, 27.71, 28.92, 29.89, 32.75, 48.48, 112.18, 113.78, 114.97, 126.30, 128.36, 129.01, 135.35, 137.63, 155.92; HRMS m/z C17H23N2S [M−I]+ calcd: 287.1576, found: 287.1576.

Workup

  1. temperatureunder reflux
  2. filtration9-heptyl-3-methyl[1,3]thiazolo[3,2-a]benzimidazol-9-ium iodide was recovered as a pale green powder (421 mg, 97%) by filtration

Sources & evidence

ORD record
ord-9703ae7875494e349bc67f58b43d9c47
Source dataset
uspto-grants-2011_03
Patent number
US07906541B2

Reaction notes

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