Ammonia → HCID 49821380, compound

HRID 74162Notes

Reaction equation

HRID 74162 reaction equation
[CH3:1][O:2][CH2:3][C:4]1[N:8]([CH:9]2[CH2:14][CH2:13][O:12][CH2:11][CH2:10]2)[C:7]2[CH:15]=[CH:16][C:17]([C:19](F)(F)F)=[CH:18][C:6]=2[N:5]=1.[NH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=1[SH:30].N>>[S:30]1[C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][C:24]=2[N:23]=[C:19]1[C:17]1[CH:16]=[CH:15][C:7]2[N:8]([CH:9]3[CH2:14][CH2:13][O:12][CH2:11][CH2:10]3)[C:4]([CH2:3][O:2][CH3:1])=[N:5][C:6]=2[CH:18]=1

Participants

4

Reactant 3

HCID 222AmmoniaHCID 87132-AminothiophenolHCID 674980032-Methoxymethyl-1-(tetrahydropyran-4-yl)-5-trifluoromethylbenzimidazole

Product 1

HCID 49821380HCID 49821380, compoundYield 8.2%

Conditions

Temperature
120 °C

Procedure

An eggplant flask was charged with 2-methoxymethyl-1-(tetrahydropyran-4-yl)-5-trifluoromethylbenzimidazole (see Working Example 6-1) (0.102 g, 0.32 mmol), 2-aminobenzenethiol (0.041 g, 0.33 mmol) and polyphosphoric acid (approx. 2 g), and this was heated to 120° C. and stirred for 48 hours. After being allowed to cool, ice was added and concentrated aqueous ammonia (28%) was added to the liquid to give approx. pH 9. Chloroform extraction, drying over anhydrous magnesium sulfate, and the solvent being distilled off gave a crude product (0.21 g), which was purified by silica gel column chromatography (MeOH/CHCl3=1/20) to yield the title compound (0.010 g, 8.1% yield) as a pale yellow powder.

Workup

  1. temperatureto cool
  2. additionice was added
  3. customto give approx. pH 9
  4. extractionChloroform extraction
  5. dry with materialdrying over anhydrous magnesium sulfate
  6. distillationthe solvent being distilled off
  7. customgave a crude product (0.21 g), which
  8. customwas purified by silica gel column chromatography (MeOH/CHCl3=1/20)

Sources & evidence

ORD record
ord-5141d5ae298041409366c4c3dcc35b96
Source dataset
uspto-grants-2014_09
Patent number
US08829035B2

Reaction notes

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