Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Ammonia | HCID 222 | — |
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | Thiocarbonyl diimidazole | HCID 11412697 | — |
| Reactant | HCID 67300937 | HCID 67300937 | — |
| Solvent | Methanol | HCID 887 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | HCID 25096341 | HCID 25096341 | — |
Reaction Steps
To a solution of 4-[5-(4-chloro-phenoxy)-pentyloxy]-2,3-dihydro-1H-indole (100 mg, 0.3 mmol) and thiocarbonyl diimidazole (64 mg, 0.36 mmol) in dry THF (3 mL) was added triethylamine (30 mg, 0.3 mmol). The reaction mixture was stirred at 50° C. for 3 hours and then 2.0 M ammonia in 4 mL methanol (excess) was added. The stirring was continued overnight at 50° C. After removal of the solvent, the residue was purified by silica gel column chromatography to give 4-[5-(4-chloro-phenoxy)-pentyloxy]-2,3-dihydro-indole-1-carbothioic acid amide, compound 8 (101 mg, 0.26 mmol, 85%) as a white solid. MS (EI): m/z 391 (M+H).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US07985763B2 |
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| Source dataset | uspto-grants-2011_07 |
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| ORD ID | ord-582d5b9b8a63477fb30429da5a937a8c |
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| Source note | uspto-grants-2011_07 |
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