Benzylamine → 6-chloro-1-hydroxy-2-(trifluoromethyl)-1H-imidazo(4,5-b)pyridine benzylamine salt

HRID 917850Notes

Reaction equation

HRID 917850 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[N:10]([OH:11])[C:9]([C:12]([F:15])([F:14])[F:13])=[N:8][C:5]2=[N:6][CH:7]=1.[CH2:16]([NH2:23])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>C(OCC)(=O)C>[CH2:16]([NH2:23])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.[Cl:1][C:2]1[CH:3]=[C:4]2[N:10]([OH:11])[C:9]([C:12]([F:13])([F:14])[F:15])=[N:8][C:5]2=[N:6][CH:7]=1

Participants

4

Reactant 2

HCID 7504BenzylamineHCID 30824181-Hydroxyfluromidine

Product 1

HCID 203554646-chloro-1-hydroxy-2-(trifluoromethyl)-1H-imidazo(4,5-b)pyridine benzylamine salt

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

6-Chloro-1-hydroxy-2-(trifluoromethyl)-1H-imidazo(4,5-b)-pyridine (1.4 grams) was mixed with 15 milliliters of ethyl acetate. The mixture was heated to reflux, and 0.6 milliliter of benzylamine was added dropwise. The mixture was then refluxed for another 30 minutes, cooled, and filtered, yielding the desired 6-chloro-1-hydroxy-2-(trifluoromethyl)-1H-imidazo(4,5-b)pyridine benzylamine salt, m.p., 200-02°C. NMR analysis in hexadeuterodimethyl sulfoxide showed a peak at 236 cps (2H); a peak at 437 cps (5H); two meta-coupled doublets at the 462 cps (1H), the other at 500 cps (1H); and a broad peak at 474 cps (3H).

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux
  3. temperatureThe mixture was then refluxed for another 30 minutes
  4. temperaturecooled
  5. filtrationfiltered

Sources & evidence

ORD record
ord-fa3245b6202f4ddcbd4874205fb17e3d
Source dataset
uspto-grants-1976_07
Patent number
US03968116

Reaction notes

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