Ammonium Chloride → HCID 178475843, compound

HRID 658101Notes

Reaction equation

HRID 658101 reaction equation
[C:1]([O-:4])(=[O:3])[CH3:2].[K+].Cl[CH2:7][C:8]1[CH:9]=[C:10]([C:14](=[O:35])[C:15](=[C:26]2[NH:30][C:29]3[CH:31]=[CH:32][CH:33]=[CH:34][C:28]=3[NH:27]2)[C:16]([C:18]2[CH:23]=[C:22]([F:24])[CH:21]=[C:20]([F:25])[CH:19]=2)=[O:17])[CH:11]=[CH:12][CH:13]=1.[Cl-].[NH4+]>CS(C)=O>[C:1]([O:4][CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([C:14](=[O:35])[C:15](=[C:26]2[NH:27][C:28]3[CH:34]=[CH:33][CH:32]=[CH:31][C:29]=3[NH:30]2)[C:16]([C:18]2[CH:23]=[C:22]([F:24])[CH:21]=[C:20]([F:25])[CH:19]=2)=[O:17])[CH:9]=1)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 517044Potassium AcetateHCID 178520862HCID 178520862, compound

Product 1

HCID 178475843HCID 178475843, compoundYield 64.4%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

After adding 35 mg of potassium acetate to 2 ml of DMSO solution containing 100 mg of 1-[3-(chloromethyl)phenyl]-3-(3,5-difluorophenyl)-2-(1,3-dihydro-2H-benzimidazol-2-ylidene)propane-1,3-dione, the mixture was stirred at room temperature for about 2 days. The reaction liquid was mixed with an appropriate amount of saturated ammonium chloride aqueous solution, extracted several times with ethyl acetate, dried with anhydrous magnesium sulfate and concentrated, and then the thus formed residue was purified by a silica gel column chromatography to obtain 90 mg of a yellow oily substance from an ethyl acetate-hexane (1:2) eluate. By crystallizing this from a small amount of ethyl acetate-hexane (1:3) at 0° C., 68 mg (64%) of 3-[3-(3,5-difluorophenyl)-2-(1,3-dihydro-2H-benzimidazol-2-ylidene)-3-oxopropanoyl]benzyl acetate (Reference Example 12-1) was obtained as yellow crystals. FA: 449

Workup

  1. customThe reaction liquid
  2. extractionextracted several times with ethyl acetate
  3. dry with materialdried with anhydrous magnesium sulfate
  4. concentrationconcentrated
  5. customthe thus formed residue was purified by a silica gel column chromatography
  6. customto obtain 90 mg of a yellow oily substance from an ethyl acetate-hexane (1:2) eluate
  7. customBy crystallizing this from a small amount of ethyl acetate-hexane (1:3) at 0° C.

Sources & evidence

ORD record
ord-645e53676d634ce0abd5db9fdacd2417
Source dataset
uspto-grants-2011_12
Patent number
US08076367B2

Reaction notes

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