Dimethylformamide → Sbb044946

HRID 1733855Notes

Reaction equation

HRID 1733855 reaction equation
[H-].[Na+].[C:3]1(C(Cl)=O)[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)C=[CH:5][CH:4]=1.O.C[CH2:18][O:19][C:20]([CH3:22])=[O:21].C[N:24](C=O)C>>[CH3:5][C:4]1[NH:24][C:7]2[C:12]([C:3]=1[CH2:22][C:20]([O:19][CH3:18])=[O:21])=[CH:11][CH:10]=[CH:9][CH:8]=2

Participants

5

Reactant 4

HCID 6228Dimethylformamide2×HCID 24758Sodium hydrideHCID 701461-Naphthalenecarbonyl chlorideHCID 22728543Water ethylacetate

Product 1

HCID 10774509Sbb044946Yield 43%

Procedure

The compound of step 1 (1.13g; 5.56 mmol) in 6 mL of DMF was treated with NaH 80% (0.18 g; 5.99 mmol) at 25° C. After 30 min a solution of 1-naphthoyl chloride in 5 mL of DMF was added dropwise The reaction mixture was left stirring for 16 h and poured into cold water-EtOAc. The organic phase was washed with H2O (2×15 mL) and brine, dried over Na2SO4 and the solvent removed. Chromatography on silica gel (eluted with 2% EtOAc in toluene) yielded 0.86 g (43%) of the title compound. 1H NMR (CDCL3, 400 MHZ) Δ2.20 (S, 3H), 3.67 (S, 3H), 7.0 (M, 1H), 7.10-7.26 (M, 3H), 7.45-7.60 (M, 5H), 7.95 (M, 1H) AND 8.07 (M, 3H).

Workup

  1. waitwas left
  2. washThe organic phase was washed with H2O (2×15 mL) and brine
  3. dry with materialdried over Na2SO4
  4. customthe solvent removed

Sources & evidence

ORD record
ord-d9dc9cb545e945a49fce9b819f3673d4
Source dataset
uspto-grants-1996_07
Patent number
US05532237

Reaction notes

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