Sodium hydride → HCID 53694173, compound

HRID 1728769Notes

Reaction equation

HRID 1728769 reaction equation
[C:1]([NH:4][CH:5]([C:16](=[O:26])[CH2:17]P(OCC)(OCC)=O)[CH2:6][C:7]1[C:8]2[CH:15]=[CH:14][CH:13]=[CH:12][C:9]=2[S:10][CH:11]=1)(=[O:3])[CH3:2].[H-].[Na+].[F:29][C:30]([F:44])([F:43])[C:31]1[CH:32]=[C:33]([CH:36]=[C:37]([C:39]([F:42])([F:41])[F:40])[CH:38]=1)[CH:34]=O>O1CCCC1>[C:1]([NH:4][CH:5]([C:16](=[O:26])[CH:17]=[CH:34][C:33]1[CH:36]=[C:37]([C:39]([F:41])([F:42])[F:40])[CH:38]=[C:31]([C:30]([F:29])([F:43])[F:44])[CH:32]=1)[CH2:6][C:7]1[C:8]2[CH:15]=[CH:14][CH:13]=[CH:12][C:9]=2[S:10][CH:11]=1)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 1362473,5-Bis(trifluoromethyl)benzaldehydeHCID 22411752HCID 22411752, compound

Product 1

HCID 53694173HCID 53694173, compoundYield 79.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of the product of step (a) (10.6 g) in dry tetrahydrofuran (200 ml) was cooled to 0° C., treated with 60% sodium hydride in oil (1.07 g) and stirred for 1 hour. 3,5-Bistrifluoromethyl benzaldehyde (6.5 g) in dry tetrahydrofuran (50 ml) was added dropwise to the reaction mixture which was stirred for 1 hour before quenching with saturated ammonium chloride. The organic layer was separated and the aqueous layer was extracted with ethyl acetate (2×100 ml). The combined organic extracts were washed with water (100 ml), dried (MgSO4), filtered and evaporated. The residue was purified by chromatography on silica using ethyl acetate/petroleum ether (bp 60-80) (2:3) to yield the title compound as a pale yellow solid (10.3 g), mp=172°-173° C.; found: C, 56.15; H, 3:54; N, 2.79; C23H17F6NO2S.0.25H2O requires C, 56.38; H, 3.60; N, 2.86%.

Workup

  1. stirringwas stirred for 1 hour
  2. custombefore quenching with saturated ammonium chloride
  3. customThe organic layer was separated
  4. extractionthe aqueous layer was extracted with ethyl acetate (2×100 ml)
  5. washThe combined organic extracts were washed with water (100 ml)
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. customevaporated
  9. customThe residue was purified by chromatography on silica

Sources & evidence

ORD record
ord-557f7102e4cc4455b480d04f3cd9e2b4
Source dataset
uspto-grants-1994_07
Patent number
US05328927

Reaction notes

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