2-Amino-5-chloro-2'-fluorobenzophenone → 2-{[2-Amino-5-chloro-alpha-(2-fluorophenyl)benzylidene]amino}ethanol

HRID 279848Notes

Reaction equation

HRID 279848 reaction equation
Cl.[CH3:2][C:3]1[NH:4]C=CN=1.[NH2:8][C:9]1[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][C:10]=1[C:11]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[F:19])=O.C(=O)(O)[O-:26].[Na+]>C(CN)O>[NH2:8][C:9]1[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][C:10]=1[C:11]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[F:19])=[N:4][CH2:3][CH2:2][OH:26]

Participants

5

Reactant 3

HCID 699122-Amino-5-chloro-2'-fluorobenzophenoneHCID 516892Sodium BicarbonateHCID 5216292-Methylimidazole hydrochloride

Product 1

HCID 233227792-{[2-Amino-5-chloro-alpha-(2-fluorophenyl)benzylidene]amino}ethanol

Reagents, catalysts & solvents 1

HCID 700EthanolamineSolvent

Procedure

A mixture of 40 g of 2-methylimidazole hydrochloride and of 90 g of 2-amino-5-chloro-2'-fluoro-benzophenone in 240 ml of ethanolamine is heated at 135° for 2 hours. After cooling, the reaction mixture is poured into an aqueous sodium bicarbonate solution. The mixture is extracted with ether, the organic phase is washed repeatedly with water and is dried over sodium sulphate, and the solvent is evaporated to dryness. The residual oil is chromatographed on a silica column, elution being carried out with a 50/50 mixture of cyclohexane and ethyl acetate.

Workup

  1. temperatureAfter cooling
  2. extractionThe mixture is extracted with ether
  3. washthe organic phase is washed repeatedly with water
  4. dry with materialis dried over sodium sulphate
  5. customthe solvent is evaporated to dryness
  6. customThe residual oil is chromatographed on a silica column, elution
  7. additionbeing carried out with a 50/50 mixture of cyclohexane and ethyl acetate

Sources & evidence

ORD record
ord-eea19af2b3f74012a5225b25d3936404
Source dataset
uspto-grants-1986_05
Patent number
US04587245

Reaction notes

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