Ammonium Hydroxide → HCID 19759748, compound

HRID 1586762Notes

Reaction equation

HRID 1586762 reaction equation
S(Cl)([Cl:3])=O.O[CH:6]([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=1[Cl:26])[CH:7]([N:15]1[CH:19]=[CH:18][N:17]=[CH:16]1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[Cl:14].[OH-].[NH4+]>C1C=CC=CC=1>[Cl:3][CH:6]([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=1[Cl:26])[CH:7]([N:15]1[CH:19]=[CH:18][N:17]=[CH:16]1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[Cl:14]

Participants

5

Reactant 3

HCID 14923Ammonium HydroxideHCID 24386Thionyl ChlorideHCID 13269112HCID 13269112, compound

Product 1

HCID 19759748HCID 19759748, compoundYield 94.8%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent2×

Procedure

A solution of 6 g (0.05 mole) of thionyl chloride dissolved in 20 ml of benzene is added dropwise to a solution containing 11 g (0.033 mole) of 1-[2-hydroxy-1,2-di-(2-chlorophenyl)ethyl] imidazole and 150 ml of benzene at room temperature. The reaction mixture is heated to reflux for 3 hours and is then made basic with 10% ammonium hydroxide solution. The organic product is extracted with ether and the combined ether extracts are washed with water, saturated sodium chloride solution, and dried over magnesium sulfate. Solvent is evaporated to give 11 g of a brown oil. This material is further purified by converting to its hydrochloride salt and back neutralized to the free base to give 8.2 g of the expected product.

Workup

  1. additionis added dropwise to a solution
  2. temperatureThe reaction mixture is heated
  3. temperatureto reflux for 3 hours
  4. extractionThe organic product is extracted with ether
  5. washthe combined ether extracts are washed with water, saturated sodium chloride solution
  6. dry with materialdried over magnesium sulfate
  7. customSolvent is evaporated

Sources & evidence

ORD record
ord-844aecbd1e3544ec8b426b3a603db480
Source dataset
uspto-grants-1993_06
Patent number
US05216007

Reaction notes

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