Bis(4-chlorophenyl)acetic acid → HCID 18475024, compound

HRID 2227884Notes

Reaction equation

HRID 2227884 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:12]2[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][CH:13]=2)[C:9]([OH:11])=O)=[CH:4][CH:3]=1.C(Cl)(=O)C(Cl)=O.[CH3:25][NH:26][CH2:27][CH2:28][OH:29].C(=O)(O)[O-].[Na+]>ClCCl.CN(C)C=O.O1CCCC1.O.C(OCC)(=O)C>[Cl:18][C:15]1[CH:16]=[CH:17][C:12]([CH:8]([C:5]2[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=2)[C:9]([N:26]([CH3:25])[CH2:27][CH2:28][OH:29])=[O:11])=[CH:13][CH:14]=1

Participants

10

Reactant 4

HCID 6730Bis(4-chlorophenyl)acetic acidHCID 80162-(Methylamino)ethanolHCID 65578Oxalyl chlorideHCID 516892Sodium Bicarbonate

Product 1

HCID 18475024HCID 18475024, compoundYield 86.4%

Reagents, catalysts & solvents 5

HCID 6228DimethylformamideCatalystHCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

A suspension of the bis(4-chlorophenyl)acetic acid (10.40 g, 36.99 mmol) in dichloromethane (100 ml) was treated with oxalyl chloride (6.2 ml, 71.07 mmol) and dimethylformamide (1 drop). The mixture was stirred at room temperature overnight and was then concentrated under vacuum and coevaporated with toluene. The residue was dissolved in tetrahydrofuran (50 ml) and this solution was added to a mixture of 2-(methylamino)ethanol (6.0 ml, 74.7 mmol) in tetrahydrofuran (100 ml), water (50 ml) and sodium bicarbonate (10 g). The reaction was stirred at room temperature for 1 hour, then diluted with ethyl acetate. This was washed with water, HCl 1N, saturated sodium bicarbonate and brine, dried over anhydrous magnesium sulfate, filtered and concentrated. The residual white solid was crystallized from ethyl acetate to give the title compound (10.81 g, 86%).

Workup

  1. concentrationwas then concentrated under vacuum
  2. dissolutionThe residue was dissolved in tetrahydrofuran (50 ml)
  3. stirringThe reaction was stirred at room temperature for 1 hour
  4. washThis was washed with water, HCl 1N, saturated sodium bicarbonate and brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residual white solid was crystallized from ethyl acetate

Sources & evidence

ORD record
ord-26afb04e619f4cd6947fd33a9aa24ab9
Source dataset
uspto-grants-2002_07
Patent number
US06414179B1

Reaction notes

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