Dimethylformamide → HCID 18319088, compound

HRID 1700928Notes

Reaction equation

HRID 1700928 reaction equation
[F:1][C:2]([F:19])([F:18])[C:3](=[O:17])[CH2:4][CH2:5][C:6]1[CH:16]=[CH:15][C:9]([O:10][CH2:11][C:12]([OH:14])=O)=[CH:8][CH:7]=1.[C:20]([Cl:25])(=O)[C:21](Cl)=O.CN(C)C=O.Cl.[Cl:32][C:33]1[CH:46]=[CH:45][C:36]([CH:37]([NH2:44])[C:38]2[CH:43]=CC=[CH:40][CH:39]=2)=[CH:35][CH:34]=1>ClCCl.O1CCCC1.C([O-])(=O)C.[Na+].C(OCC)(=O)C>[Cl:32][C:33]1[CH:34]=[CH:35][C:36]([CH:37]([C:38]2[CH:43]=[CH:21][C:20]([Cl:25])=[CH:40][CH:39]=2)[NH:44][C:12](=[O:14])[CH2:11][O:10][C:9]2[CH:8]=[CH:7][C:6]([CH2:5][CH2:4][C:3](=[O:17])[C:2]([F:1])([F:19])[F:18])=[CH:16][CH:15]=2)=[CH:45][CH:46]=1

Participants

9

Reactant 4

HCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 162190964-Chlorobenzhydrylamine hydrochlorideHCID 18319061HCID 18319061, compound

Product 1

HCID 18319088HCID 18319088, compoundYield 87.5%

Reagents, catalysts & solvents 4

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolventHCID 517045Sodium AcetateSolvent

Procedure

A solution of 4-(4,4,4-trifluoro-3-oxo-1-butyl)phenoxyacetic acid (0.374 g, 1.35 mmol) in dichloromethane (10 ml) was treated with oxalyl chloride (0.17 ml, 2.03 mmol) and a trace of N,N-dimethylformamide. After 30 min at 22° C., the solvent and excess reagent were evaporated under reduced pressure and the residual oil obtained was dissolved in anhydrous tetrahydrofuran (10 ml). This solution was then added dropwise to a vigorously stirred solution of p-chlorobenzhydrylamine hydrochloride (0.39 g, 1.35 mmol) in a mixture of tetrahydrofuran (10 ml) and 40% aqueous sodium acetate (10 ml). After 30 min at 22° C., the reaction mixture was diluted with ethyl acetate, washed with water, brine and dried. Evaporation of the solvent under reduced pressure gave a solid which was chromatographed on silica gel. Elution with a mixture of toluene and ethyl acetate (8:2) gave 0.603 g (87%) of the title product as white crystals: mp 145-146° C.

Workup

  1. customthe solvent and excess reagent were evaporated under reduced pressure
  2. customthe residual oil obtained
  3. waitAfter 30 min at 22° C.
  4. washwashed with water, brine
  5. customdried
  6. customEvaporation of the solvent under reduced pressure
  7. customgave a solid which
  8. customwas chromatographed on silica gel
  9. washElution
  10. additionwith a mixture of toluene and ethyl acetate (8:2)

Sources & evidence

ORD record
ord-7babdbaa2d7a49df9067a55322eb059a
Source dataset
uspto-grants-2002_02
Patent number
US06350892B1

Reaction notes

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