Sodium Bicarbonate → HCID 67530789, compound

HRID 602582Notes

Reaction equation

HRID 602582 reaction equation
[I-].[F:2][C:3]1[CH:15]=[CH:14][C:6]2[N:7]3[C:12]([CH3:13])=[CH:11][S:10][C:8]3=[NH+:9][C:5]=2[CH:4]=1.C([O-])(O)=O.[Na+]>>[F:2][C:3]1[CH:15]=[CH:14][C:6]2[N:7]3[C:12]([CH3:13])=[CH:11][S:10][C:8]3=[N:9][C:5]=2[CH:4]=1

Participants

3

Reactant 2

HCID 516892Sodium BicarbonateHCID 178431878HCID 178431878, compound

Product 1

HCID 67530789HCID 67530789, compoundYield 75.4%

Procedure

1 g (2.99 mmol) of 7-fluoro-3-methyl[1,3]thiazolo[3,2-a]benzimidazol-9-ium iodide obtained in stage B2 was poured in a NaHCO3 saturated aqueous solution (50 mL). The mixture was extracted 3×50 mL of CH2Cl2; the organic layer was dried with MgSO4 and evaporated under reduced pressure to yield 7-fluoro-3-methyl[1,3]thiazolo[3,2-a]benzimidazole (465 mg, yellow powder, 75%). Mp=148° C.; 1H NMR (300 MHz, CDCl3) δ=2.68 (3H, d, J=0.8, CH3), 6.34 (1H, q, J=0.8, H5), 6.91-7.66 (3H, in, Ar); 13C NMR (75 MHz, CDCl3) δ=14.3, 104.8, 104.9 (d, J=23), 108.7 (d, J=26), 110.6 (d, J=10), 126.9, 129.7, 149.0 (d, J=12), 158.5, 159.6 (d, J=239); HRMS m/z C10H8N2FS [M+H]+ calcd: 207.0387, found: 207.0386 400 mg (1.94 mmol) of 7-fluoro-3-methyl[1,3]thiazolo[3,2-a]benzimidazole were solubilised in acetone (10 mL), then CH3I (10 eq, 1.2 mL) was added and the solution stirred at r.t. for 12 h. 7-Fluoro-3-methyl[1,3]thiazolo[3,2-a]benzimidazol-9-ium iodide was recovered by filtration (white powder, 641 mg, 95%). Mp=>270° C.; 1H NMR (300 MHz, DMSO-d6) δ=2.86 (3H, d, J=1.3, CH3), 4.09 (3H, s, NCH3), 7.46 (1H, q, J=1.3, H5), 7.51-7.58 (1H, in, Ar), 8.09-8.12 (1H, m, Ar), 8.28-8.33 (1H, m, Ar); 13C NMR (75 MHz, DMSO-d6) δ=13.43, 33.22, 100.23 (d, J=29), 112.25, 112.51 (d, J=26), 115.47 (d, J=10), 126.67 (d, J=1), 133.02, 137.37 (d, J=14), 156.10, 160.45 (d, J=244); HRMS m/z C11H10N2FS [M−I]+ calcd: 221.0543, found: 221.0546.

Workup

  1. extractionThe mixture was extracted 3×50 mL of CH2Cl2
  2. dry with materialthe organic layer was dried with MgSO4
  3. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-573bbda7309049bcb6ea98474aa86fd5
Source dataset
uspto-grants-2011_03
Patent number
US07906541B2

Reaction notes

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