Ammonia → HCID 14518706, compound

HRID 1723146Notes

Reaction equation

HRID 1723146 reaction equation
N#N.C1(C[C:10]2[C:15]([CH2:16][N:17]3[CH:21]=[CH:20][N:19]=[CH:18]3)=[CH:14][CH:13]=[C:12]([NH2:22])[C:11]=2[NH2:23])CCCCC1.[F:24][C:25]([F:31])([F:30])[C:26](=N)OC.F[C:33](F)(F)[C:34](O)=O.N>CO>[CH:34]1([CH2:33][N:23]2[C:11]3[CH:10]=[C:15]([CH2:16][N:17]4[CH:21]=[CH:20][N:19]=[CH:18]4)[CH:14]=[CH:13][C:12]=3[N:22]=[C:26]2[C:25]([F:31])([F:30])[F:24])[CH2:14][CH2:15][CH2:10][CH2:11][CH2:12]1

Participants

6

Reactant 4

HCID 222AmmoniaHCID 6422Trifluoroacetic acidHCID 256220methyl 2,2,2-trifluoroethanimidateHCID 86743323HCID 86743323, compound

Product 1

HCID 14518706HCID 14518706, compoundYield 52.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

A mixture of 2.75 parts of N2 -(cyclohexylmethyl)-4-(1H-imidazol-1-ylmethyl)-1,2-benzenediamine, 1.85 parts of methyl 2,2,2-trifluoroethanimidate, 40 parts of methanol and 2.3 parts of trifluoroacetic acid was stirred for 7 hours at room temperature. The reaction mixture was made alkaline with methanol, saturated with ammonia. The solvent was evaporated in vacuo and the residue was purified by column chromatography over silica gel using a mixture of trichloromethane and methanol (95:5 by volume) as eluent. The pure fractions were collected and the eluent was evaporated in vacuo. The residue was dissolved in 11 parts of 2,2'-oxybispropane. The crystallized product was filtered off and dried, yielding 1.9 parts (52.4%) of 1-(cyclohexylmethyl)-6-(1H-imidazol-1-ylmethyl)-2-(trifluoromethyl)-1H-benzimidazole; mp. 165.4° C. (compound 202).

Workup

  1. customThe solvent was evaporated in vacuo
  2. customthe residue was purified by column chromatography over silica gel using
  3. additiona mixture of trichloromethane and methanol (95:5 by volume) as eluent
  4. customThe pure fractions were collected
  5. customthe eluent was evaporated in vacuo
  6. dissolutionThe residue was dissolved in 11 parts of 2,2'-oxybispropane
  7. filtrationThe crystallized product was filtered off
  8. customdried

Sources & evidence

ORD record
ord-c0b00f770d3d46c1b1acbb7d7c765b64
Source dataset
uspto-grants-1989_08
Patent number
US04859684

Reaction notes

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