Diisopropylethylamine → HCID 54449557, compound

HRID 976258Notes

Reaction equation

HRID 976258 reaction equation
[C:1]([O:5][C:6]([NH:8][CH:9]([C:20](=[O:28])[CH2:21]P(OC)(OC)=O)[CH2:10][C:11]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[NH:13][CH:12]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(N(C(C)C)CC)(C)C.[Cl-].[Li+].[F:40][C:41]([F:55])([F:54])[C:42]1[CH:43]=[C:44]([CH:47]=[C:48]([C:50]([F:53])([F:52])[F:51])[CH:49]=1)[CH:45]=O>C(#N)C>[F:40][C:41]([F:54])([F:55])[C:42]1[CH:43]=[C:44]([CH:45]=[CH:21][C:20](=[O:28])[CH:9]([NH:8][C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:7])[CH2:10][C:11]2[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[NH:13][CH:12]=2)[CH:47]=[C:48]([C:50]([F:51])([F:52])[F:53])[CH:49]=1

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 1362473,5-Bis(trifluoromethyl)benzaldehydeHCID 433294Lithium ChlorideHCID 15238182HCID 15238182, compound

Product 1

HCID 54449557HCID 54449557, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

A solution of the product of part (b) (69.0 g) in acetonitrile (600 ml) was stirred with diisopropylethylamine (43.3 g), and anhydrous lithium chloride (14.13 g) for 30 minutes before adding 3,5-bistrifluoromethylbenzaldehyde (55 g) in acetonitrile (200 ml). The reaction was stirred for two hours then the solvent was removed and the residue partitioned between ethyl acetate and water. The organic phase was washed with 10% citric acid (500 ml), water (500 ml), saturated sodium bicarbonate (500 ml) and water (500 ml). The solution was dried (MgSO4), filtered and evaporated. The residue was purified by column chromatography on silica using ethyl acetate/petroleum ether (1:4) to yield the title compound as a pale yellow solid, mp=137°-138° C.; found: C, 59.23; H, 4.79; N, 5.35; C26H24F6N2O3 requires C, 59.32; H, 4.60; N 5.32%.

Workup

  1. customthe solvent was removed
  2. customthe residue partitioned between ethyl acetate and water
  3. washThe organic phase was washed with 10% citric acid (500 ml), water (500 ml), saturated sodium bicarbonate (500 ml) and water (500 ml)
  4. dry with materialThe solution was dried (MgSO4)
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue was purified by column chromatography on silica

Sources & evidence

ORD record
ord-bc0eea1402a042ed81aac562c2434668
Source dataset
uspto-grants-1997_03
Patent number
US05612336

Reaction notes

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