Ammonia → HCID 178503642, compound

HRID 1108352Notes

Reaction equation

HRID 1108352 reaction equation
[CH3:1][S:2][C:3]1[S:4][C:5]([C:21]([O:23]CC)=O)=[C:6]2[CH2:20][CH2:19][C:9]3[N:10]=[C:11]([C:13]4[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=4)[NH:12][C:8]=3[C:7]=12.[NH3:26].O>CO.O1CCCC1>[CH3:1][S:2][C:3]1[S:4][C:5]([C:21]([NH2:26])=[O:23])=[C:6]2[CH2:20][CH2:19][C:9]3[N:10]=[C:11]([C:13]4[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=4)[NH:12][C:8]=3[C:7]=12

Participants

6

Reactant 3

HCID 222AmmoniaHCID 962WaterHCID 178470566Ethyl 4,5-dihydro-8-methylthio-2-phenylthieno(3,4-e]benzimidazole-6-carboxylate

Product 1

HCID 178503642HCID 178503642, compoundYield 14%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of ethyl 4,5-dihydro-8-methylthio-2-phenylthieno[3,4-e]benzimidazole-6-carboxylate (0.50 g), a 10% (w/w) ammonia solution (30 ml) in methanol and tetrahydrofuran (30 ml) was heated in a sealed tube at 100° C. for 3 days. The reaction mixture was poured over water and extracted with ethyl acetate-tetrahydrofuran (3:1, v/v). The organic layer was washed with water and dried (MgSO4), after which the solvent was distilled off. The residue was subjected to silica gel column chromatography and eluted with chloroform-methanol (30:1, v/v) to yield 4,5-dihydro-8-methylthio-2-phenylthieno[3,4-e]benzimidazole-6-carboxamide (65 mg, 14%), which was then recrystallized from ethanol. Colorless prisms. Melting point 206-207° C.

Workup

  1. extractionextracted with ethyl acetate-tetrahydrofuran (3:1, v/v)
  2. washThe organic layer was washed with water
  3. dry with materialdried (MgSO4)
  4. distillationafter which the solvent was distilled off
  5. washeluted with chloroform-methanol (30:1, v/v)

Sources & evidence

ORD record
ord-06bc56d889a548e180d60aa0edb63518
Source dataset
uspto-grants-2000_05
Patent number
US06066658

Reaction notes

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