Hydrochloric Acid → HCID 178498014, compound

HRID 2292651Notes

Reaction equation

HRID 2292651 reaction equation
[N+:1]([C:4]1[CH:13]=[CH:12][C:7]2[NH:8][C:9]([SH:11])=[N:10][C:6]=2[CH:5]=1)([O-:3])=[O:2].[CH3:14][O:15][C:16](=[O:25])[C:17]1[CH:22]=[CH:21][C:20]([CH2:23]Br)=[CH:19][CH:18]=1.C(N(CC)CC)C.Cl>CO.C(O)C>[CH3:14][O:15][C:16](=[O:25])[C:17]1[CH:22]=[CH:21][C:20]([CH2:23][S:11][C:9]2[NH:8][C:7]3[CH:12]=[CH:13][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][C:6]=3[N:10]=2)=[CH:19][CH:18]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 256687Methyl 4-(bromomethyl)benzoateHCID 178526489HCID 178526489, compound

Product 1

HCID 178498014HCID 178498014, compoundYield 41%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 887MethanolSolvent

Procedure

A mixture of 5-nitro-1H-benzoimidazol-2-thiol (1.95 g, 0.01 mol), 4-bromomethyl-benzoic acid methyl ester (2.29 g, 0.01 mol), triethylamine (2 mL), and ethanol (100 mL) was heated at reflux for a period of 4.5 hours. The solvent was evaporated. The residue was dissolved in ethyl acetate and washed with water. The organic phase was evaporated. The residue was crystallized from ethyl acetate/hexane. The solid obtained was dissolved in methanol and the solution was saturated with hydrogen chloride. The methanol was evaporated. The residue was treated with ethyl acetate. The solid was collected to give the title compound (1.4 g, 41%) as a mono-hydrochloride, white solid, m.p. 228°-230° (dec.). Anal. Calcd. for C16H13N3O4S.HCl: C, 50.60; H, 3.72; N, 11.06. Found: C, 50.82; H, 3.68; N, 10.92. Mass spectrum (+FAB; [M+H]+) 344. 1H-NMR (DMSO-d6 ; 400 MHz) δ 8.32 (s, 1H), 8.06 (d, 1H), 7.88 (d, 2H), 7.62 (m, 3H), 5.0-7.4 f(br s, 4H), 4.67 (s, 2H), and 3.81 ppm (s, 3H).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for a period of 4.5 hours
  3. customThe solvent was evaporated
  4. dissolutionThe residue was dissolved in ethyl acetate
  5. washwashed with water
  6. customThe organic phase was evaporated
  7. customThe residue was crystallized from ethyl acetate/hexane
  8. customThe solid obtained
  9. customThe methanol was evaporated
  10. additionThe residue was treated with ethyl acetate
  11. customThe solid was collected

Sources & evidence

ORD record
ord-4b61b9339e734b94a195f2436bb95d1a
Source dataset
uspto-grants-1997_11
Patent number
US05684030

Reaction notes

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