Potassium Carbonate → HCID 19858592, compound

HRID 2072605Notes

Reaction equation

HRID 2072605 reaction equation
[Cl:1][C:2]1[CH:20]=[C:19]([C:21]([F:24])([F:23])[F:22])[CH:18]=[CH:17][C:3]=1[O:4][C:5]1[CH:10]=[CH:9][C:8]([N+:11]([O-:13])=[O:12])=[C:7]([N+:14]([O-])=O)[CH:6]=1.Cl.[NH2:26][CH2:27][C:28]#N.C(=O)([O-])[O-].[K+].[K+].O1CCOCC1>O>[Cl:1][C:2]1[CH:20]=[C:19]([C:21]([F:24])([F:23])[F:22])[CH:18]=[CH:17][C:3]=1[O:4][C:5]1[CH:10]=[CH:9][C:8]([N+:11]([O-:13])=[O:12])=[C:7]([NH:14][CH2:28][C:27]#[N:26])[CH:6]=1

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 312751,4-DioxaneHCID 156238Benzene, 2-chloro-1-(3,4-dinitrophenoxy)-4-(trifluoromethyl)-HCID 11491918Aminoacetonitrile hydrochloride

Product 1

HCID 19858592HCID 19858592, compoundYield 15.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Into a flask equipped with a reflux condenser, magnetic stirrer, nitrogen inlet and heating mantle, there was added 4-(2-chloro-4-(trifluoromethyl)-phenoxy)-1,2-dinitrobenzene (5 gm, 0.014 mol), aminoacetonitrile hydrochloride (5.1 gm, 0.055 mol), anhydrous potassium carbonate (7.4 gm, 0.053 formula weight) and 50 ml of dioxane. The solution was sirred and refluxed overnight, cooled and poured into water. Following ether extraction, the organic layer was dried and evaporated to a residue. The residual material was chromatographed over silica gel using 15% acetone and 85% hexane as the eluant to yield 800 mg of the desired product.

Workup

  1. customInto a flask equipped with a reflux condenser, magnetic stirrer, nitrogen inlet
  2. temperatureheating mantle, there
  3. temperaturerefluxed overnight
  4. temperaturecooled
  5. extractionFollowing ether extraction
  6. customthe organic layer was dried
  7. customevaporated to a residue
  8. customThe residual material was chromatographed over silica gel using 15% acetone and 85% hexane as the eluant

Sources & evidence

ORD record
ord-a64ed04e10304e31bd6a182462208d3b
Source dataset
uspto-grants-1990_04
Patent number
US04913729

Reaction notes

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