Triethylamine → HCID 21829909, compound

HRID 1600547Notes

Reaction equation

HRID 1600547 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C:20]1([CH:26]2[S:30][CH2:29][N:28]([C:31]([CH3:36])([CH3:35])[C:32]([OH:34])=O)[C:27]2=[O:37])[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.[F:38][C:39]1[CH:45]=[CH:44][C:43]([F:46])=[CH:42][C:40]=1[NH2:41].C(N(CC)CC)C>C(Cl)(Cl)(Cl)Cl.ClCCl.C(Cl)(Cl)Cl>[F:38][C:39]1[CH:45]=[CH:44][C:43]([F:46])=[CH:42][C:40]=1[NH:41][C:32](=[O:34])[C:31]([N:28]1[C:27](=[O:37])[CH:26]([C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)[S:30][CH2:29]1)([CH3:36])[CH3:35]

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 11776TriphenylphosphineHCID 677752,5-DifluoroanilineHCID 21829903HCID 21829903, compound

Product 1

HCID 21829909HCID 21829909, compoundYield 43.2%

Reagents, catalysts & solvents 3

HCID 5943Carbon TetrachlorideSolventHCID 6212ChloroformSolventHCID 6344DichloromethaneSolvent

Procedure

Triphenylphosphine (1.93 g) was added to a suspension of 2-(5-phenylthiazolidin-4-on-3-yl)isobutyric acid (1.5 g) prepared according to Example 12 in carbon tetrachloride (15 mL) and dichloromethane (15 mL), and the mixture was heated for 40 minutes at 70° C. The reaction mixture was cooled with ice-water, to which 2,5-difluoroaniline (0.73 g) and then triethylamine (0.57 g) were added, and the mixture was stirred for 3 days at room temperature. The reaction mixture was diluted with chloroform, and then sequentially washed with water, diluted hydrochloric acid and a saturated sodium hydrogencarbonate aqueous solution, and dried over anhydrous sodium sulfate. After distilling off the solvent under reduced pressure, the resulting crude product was purified by preparative thin-layer chromatography (developing solvent: chloroform/ethyl acetate=10/1) to give 0.92 g of the title compound as viscous oil.

Workup

  1. customprepared
  2. washsequentially washed with water, diluted hydrochloric acid
  3. dry with materiala saturated sodium hydrogencarbonate aqueous solution, and dried over anhydrous sodium sulfate
  4. distillationAfter distilling off the solvent under reduced pressure
  5. customthe resulting crude product was purified by preparative thin-layer chromatography (developing solvent: chloroform/ethyl acetate=10/1)

Sources & evidence

ORD record
ord-47b81839243d4c69893d0d12adda93ce
Source dataset
uspto-grants-1999_11
Patent number
US05977027

Reaction notes

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