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Sodium Iodide → HCID 58622877, compound

HRID 1269654
Notes
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Reaction equation

HRID 1269654 reaction equation
Cl[CH2:2][C:3]1[CH:15]=[CH:14][C:6]([O:7][CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10])=[C:5]([CH3:16])[CH:4]=1.[I-].[Na+].[CH2:19]([NH:23][C:24]1[C:25]([CH3:37])=[C:26]([C:30]2[CH:35]=[CH:34][C:33]([CH3:36])=[CH:32][CH:31]=2)[CH:27]=[CH:28][CH:29]=1)[CH2:20][CH2:21][CH3:22]>C(#N)C>[CH2:19]([N:23]([CH2:2][C:3]1[CH:15]=[CH:14][C:6]([O:7][CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10])=[C:5]([CH3:16])[CH:4]=1)[C:24]1[C:25]([CH3:37])=[C:26]([C:30]2[CH:35]=[CH:34][C:33]([CH3:36])=[CH:32][CH:31]=2)[CH:27]=[CH:28][CH:29]=1)[CH2:20][CH2:21][CH3:22]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 5238Sodium IodideHCID 16109205HCID 16109205, compoundHCID 18448422HCID 18448422, compound

Product 1

HCID 58622877HCID 58622877, compoundYield 78.6%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

Ethyl [4-(chloromethyl)-2-methylphenoxy]acetate (35.9 g, 0.148 mols) was dissolved in dry acetonitrile (285 mL). Sodium iodide (20.1 g, 0.135 mols 1 eq) was added in one portion and mixture stirred for 5 mins. A solution of the N-butyl-N-(2,4′-dimethyl-1,1′-biphenyl-3-yl)amine (34 g. 0.135 mol) and disopropylethylamine (23.5 mL, 0.135 mol) in dry acetonitrile (285 mL) was added over 10 min and cooling applied to maintain reaction temperature at ca. 16° C. during the addition. The reaction was concentrated in vacuo and the resultant orange oil partitioned between DCM (700 mL) and water (700 mL). The aqueous was extracted with DCM (500 mL) and the combined organic extracts were cautiously washed with brine (300 mL). After drying (Na2SO4) the mixture was concentrated in vacuo to give a dark orange oil. Purification using flash chromatography on (2 kg silica column), eluting with 1:1–0:1 cyclohexane:DCM afforded the title compound as a yellow oil (48.8 g).

Workup

  1. temperaturecooling
  2. temperatureto maintain
  3. customreaction temperature at ca. 16° C.
  4. additionduring the addition
  5. concentrationThe reaction was concentrated in vacuo
  6. customthe resultant orange oil partitioned between DCM (700 mL) and water (700 mL)
  7. extractionThe aqueous was extracted with DCM (500 mL)
  8. washthe combined organic extracts were cautiously washed with brine (300 mL)
  9. dry with materialAfter drying (Na2SO4) the mixture
  10. concentrationwas concentrated in vacuo
  11. customto give a dark orange oil
  12. customPurification
  13. washeluting with 1:1–0:1 cyclohexane

Sources & evidence

ORD record
ord-10b7a9e7dc0b4cda912d2c73e9aee2db
Source dataset
uspto-grants-2007_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07199239B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes