Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Ammonia | HCID 222 | — |
| Reactant | L-Lactic Acid | HCID 107689 | — |
| Reactant | HCID 63226205 | HCID 63226205 | — |
| Solvent | Hydrochloric Acid | HCID 313 | — |
| Product | HCID 89933262 | HCID 89933262 | 63% |
Reaction Steps
A mixture of 4-chloro-N1-(3,3,3-trifluoropropyl)benzene-1,2-diamine (478 mg, 2.0 mmol) and L-lactic acid (180 mg, 2.0 mmol) in 6 N aqueous HCl (4 mL) was heated with stirring at 100° C. in a sealed tube for 18 hours. After the reaction was complete, the mixture was poured into aqueous ammonia (10 mL) and then extracted by EtOAc (25 mL×3). The organic layers were combined and then concentrated in vacuo. The residue was purified by flash column chromatography to afford (1S)-1-[5-chloro-1-(3,3,3-trifluoropropyl)-1H-benzimidazol-2-yl]ethanol as yellow oil (320 mg, yield 63.0%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US09206191B2 |
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| Source dataset | uspto-grants-2015_12 |
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| ORD ID | ord-d5d5ffc320614b01bc3adf8ed25443fd |
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| Source note | uspto-grants-2015_12 |
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