Acetic Acid → HCID 18512033, compound

HRID 1370787Notes

Reaction equation

HRID 1370787 reaction equation
C(O)(=O)C.[CH2:5]([NH:12][C:13]1[C:14]([CH3:24])=[C:15]([NH:19][S:20]([CH3:23])(=[O:22])=[O:21])[CH:16]=[CH:17][CH:18]=1)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.[N+:25]([C:28]1[CH:35]=[CH:34][C:31]([CH:32]=O)=[CH:30][CH:29]=1)([O-:27])=[O:26].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C([O-])(O)=O.[Na+]>ClC(Cl)C.CC#N>[CH2:5]([N:12]([CH2:32][C:31]1[CH:34]=[CH:35][C:28]([N+:25]([O-:27])=[O:26])=[CH:29][CH:30]=1)[C:13]1[C:14]([CH3:24])=[C:15]([NH:19][S:20]([CH3:23])(=[O:22])=[O:21])[CH:16]=[CH:17][CH:18]=1)[C:6]1[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=1

Participants

8

Reactant 5

HCID 176Acetic AcidHCID 5414-NitrobenzaldehydeHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 18512172HCID 18512172, compound

Product 1

HCID 18512033HCID 18512033, compoundYield 5%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 63651,1-DichloroethaneSolvent

Procedure

Glacial acetic acid (0.37 mL, 6.4 mmoles) was added to a solution of Example 8A (0.46 g, 1.6 mmoles) and 4-nitrobenzaldehyde (0.48 g, 3.2 mmoles) in dichloroethane (3.2 mL) and CH3CN (4.0 mL). The reaction was stirred for 4 hours at room temperature and was treated with sodium triacetoxyborohydride (0.68 g, 3.2 mmoles). The reaction mixture was stirred overnight at room temperature. The mixture was poured into saturated aqueous NaHCO3 (150 mL) and extracted with diethyl ether (150 mL). The organic phase was washed with brine (150 mL), dried (Na2SO4), filtered, and the filtrate concentrated under reduced pressure. The residue was purified by flash chromatography (5:2→1:1 hexanes:ethyl acetate) to provide the title compound as a brown solid (0.034 g, 5% yield). 1H NMR (300 MHz, CDCl3) δ8.12 (d, J=8.9 Hz, 2H), 7.37 (d, J=8.9 Hz, 2H), 7.27 (m, 6H), 7.12 (t, J=7.8 Hz, 1H), 6.87 (d, J=8.1 Hz, 1H), 6.14 (s, 1H), 4.18 (s, 2H), 4.06 (s, 2H), 2.99 (s, 3H), 2.38 (s, 3H); MS (APCI+) m/z 426 (M+H)+.

Workup

  1. stirringThe reaction mixture was stirred overnight at room temperature
  2. extractionextracted with diethyl ether (150 mL)
  3. washThe organic phase was washed with brine (150 mL)
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationthe filtrate concentrated under reduced pressure
  7. customThe residue was purified by flash chromatography (5:2→1:1 hexanes:ethyl acetate)

Sources & evidence

ORD record
ord-41d293c653e842379612625cdb24c579
Source dataset
uspto-grants-2003_06
Patent number
US06583180B2

Reaction notes

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