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Water → Ibrolipim

HRID 650502
Notes
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Reaction equation

HRID 650502 reaction equation
[NH2:1][C:2]1[CH:9]=[CH:8][C:7]([Br:10])=[CH:6][C:3]=1[C:4]#[N:5].C(N(CC)CC)C.[CH2:18]([O:20][P:21]([CH2:26][C:27]1[CH:35]=[CH:34][C:30]([C:31](Cl)=[O:32])=[CH:29][CH:28]=1)([O:23][CH2:24][CH3:25])=[O:22])[CH3:19].O>CN(C)C1C=CN=CC=1.ClCCl>[Br:10][C:7]1[CH:8]=[CH:9][C:2]([NH:1][C:31]([C:30]2[CH:34]=[CH:35][C:27]([CH2:26][P:21](=[O:22])([O:20][CH2:18][CH3:19])[O:23][CH2:24][CH3:25])=[CH:28][CH:29]=2)=[O:32])=[C:3]([C:4]#[N:5])[CH:6]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 4297402-Amino-5-bromobenzonitrileHCID 104469734-[(Diethoxyphosphoryl)-methyl]benzoyl chloride

Product 1

HCID 131601IbrolipimYield 32.6%

Reagents, catalysts & solvents 2

HCID 14284
4-(Dimethylamino)pyridine
Catalyst
HCID 6344DichloromethaneSolvent2×

Procedure

3.94 Grams (20 millimoles) of 2-amino-5-bromo-benzonitrile, 2.22 g (22 millimoles) of triethylamine and 0.49 g (4 millimoles) of 4-dimethylaminopyridine were dissolved in 40 ml of dry dichloromethane, under ice-cooling there was added dropwise slowly 40 ml of dry dichloromethane solution of 5.81 g (20 millimoles) of 4-diethoxyphosphorylmethylbenzoyl chloride with stirring. The reaction was carried out at room temperature for 10 hours, to this reaction mixture was added 50 ml of water, then extracted with chloroform and the organic layer was dried over anhydrous sodium sulfate, next the solvent was removed by distillation under reduced pressure. Thus obtained residue was refined by means of a silica gel column chromatography (eluted with chloroform: ethyl acetate=1:2), recrystallized from benzen-n-hexane, there was obtained 2.94 g of diethyl 4-[N-(4-bromo-2-cyanophenyl)carbamoyl]benzylphosphonate as colorless crystals.

Workup

  1. temperaturecooling there
  2. extractionextracted with chloroform
  3. dry with materialthe organic layer was dried over anhydrous sodium sulfate, next the solvent
  4. customwas removed by distillation under reduced pressure
  5. washThus obtained residue was refined by means of a silica gel column chromatography (eluted with chloroform: ethyl acetate=1:2)
  6. customrecrystallized from benzen-n-hexane

Sources & evidence

ORD record
ord-3e858a521f0046a8b3e02947674c4abf
Source dataset
uspto-grants-2001_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06274571B1

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes