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Dimethylformamide → HCID 53957464, compound

HRID 1756772
Notes
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Reaction equation

HRID 1756772 reaction equation
[CH:1]([C:4]1[CH:11]=[CH:10][CH:9]=[C:8]([CH:12]([CH3:14])[CH3:13])[C:5]=1[CH2:6]Cl)([CH3:3])[CH3:2].[C:15]1(=[O:25])[NH:19][C:18](=[O:20])[C:17]2=[CH:21][CH:22]=[CH:23][CH:24]=[C:16]12.[K].CN(C)C=O>O>[CH:1]([C:4]1[CH:11]=[CH:10][CH:9]=[C:8]([CH:12]([CH3:14])[CH3:13])[C:5]=1[CH2:6][N:19]1[C:18](=[O:20])[C:17]2=[CH:21][CH:22]=[CH:23][CH:24]=[C:16]2[C:15]1=[O:25])([CH3:3])[CH3:2]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 24194345Phthalimide potassium saltHCID 54108381HCID 54108381, compound

Product 1

HCID 53957464HCID 53957464, compoundYield 71.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of 0.92 g (4.4 mmol) of 2, 6-diisopropylbenzyl chloride, 0.97 g (5.24 mmol) of potassium phthalimide and 8 ml of N, N-dimethylformamide was stirred at 70° C. for 1.5 hours. After cooling, the reaction mixture was mixed with water and extracted with ethyl acetate. The extract was washed with saturated saline, dried over anhydrous magnesium sulfate and the solvent evaporated in vacuo. The residue was mixed with 15 ml of hexane and 2 ml of ethyl acetate, stirred at room temperature, and the precipitated crystals were filtered to give 1.01 g of N-(2, 6-diisopropylbenzyl)-phthalimide.

Workup

  1. temperatureAfter cooling
  2. extractionextracted with ethyl acetate
  3. washThe extract was washed with saturated saline
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customthe solvent evaporated in vacuo
  6. additionThe residue was mixed with 15 ml of hexane and 2 ml of ethyl acetate
  7. stirringstirred at room temperature
  8. filtrationthe precipitated crystals were filtered

Sources & evidence

ORD record
ord-16c9a2ebf6844efe82e37f642057af9b
Source dataset
uspto-grants-1995_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05442060

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes