Ammonia → HCID 89933262, compound

HRID 1500952Notes

Reaction equation

HRID 1500952 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([NH2:15])[C:5]([NH:8][CH2:9][CH2:10][C:11]([F:14])([F:13])[F:12])=[CH:6][CH:7]=1.[C:16](O)(=O)[C@H:17]([CH3:19])[OH:18].N>Cl>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]2[N:8]([CH2:9][CH2:10][C:11]([F:12])([F:14])[F:13])[C:16]([C@@H:17]([OH:18])[CH3:19])=[N:15][C:4]=2[CH:3]=1

Participants

5

Reactant 3

HCID 222AmmoniaHCID 107689L-Lactic AcidHCID 63226205HCID 63226205, compound

Product 1

HCID 89933262HCID 89933262, compoundYield 63%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Conditions

Temperature
100 °C

Procedure

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%).

Workup

  1. temperaturewas heated
  2. extractionextracted by EtOAc (25 mL×3)
  3. concentrationconcentrated in vacuo
  4. customThe residue was purified by flash column chromatography

Sources & evidence

ORD record
ord-d5d5ffc320614b01bc3adf8ed25443fd
Source dataset
uspto-grants-2015_12
Patent number
US09206191B2

Reaction notes

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