Sodium hydride → HCID 59011464, compound

HRID 1991022Notes

Reaction equation

HRID 1991022 reaction equation
[C:1]([C:3]([C:16]1[CH:21]=[CH:20][C:19]([N+:22]([O-:24])=[O:23])=[CH:18][CH:17]=1)([CH2:10][CH2:11][C:12]([O:14][CH3:15])=[O:13])[CH2:4][CH2:5][C:6]([O:8]C)=O)#[N:2].[H-].[Na+]>COCCOC>[C:1]([C:3]1([C:16]2[CH:17]=[CH:18][C:19]([N+:22]([O-:24])=[O:23])=[CH:20][CH:21]=2)[CH2:10][CH:11]([C:12]([O:14][CH3:15])=[O:13])[C:6](=[O:8])[CH2:5][CH2:4]1)#[N:2]

Participants

4

Reactant 2

HCID 24758Sodium hydrideHCID 59011458HCID 59011458, compound

Product 1

HCID 59011464HCID 59011464, compoundYield 102.2%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

To a solution of 2 (88.96 g, 0.27 mol) in DME (1 L) at RT under N2 was added (carefully) NaH (60% in mineral oil, 31.92 g, 0.80 mol) to give a dark violet solution. The reaction was heated at reflux for 4 h, was cooled and quenched carefully with H2O, acidified with 2N HCl and extracted with 2×EtOAc. The combined organics were washed with saturated NaCl solution, dried over a mixture of activated charcoal and Na2SO4, filtered through Celite and evaporated to give crude product 3 as a brown solid (83.42 g, >100%). 1H-NMR (500 MHz, dmso-d6) 12.1 (s, 1H), 8.31 (d, 2H), 7.88 (d, 2H), 3.75 (s, 3H), 2.86 (AB quartet, 2H), 2.65 (m, 1H), 2.6 (m, 1H), 2.4 (m, 1H), 2.35 (m, 1H) ppm.

Workup

  1. customto give a dark violet solution
  2. temperatureThe reaction was heated
  3. temperatureat reflux for 4 h
  4. temperaturewas cooled
  5. customquenched carefully with H2O
  6. extractionextracted with 2×EtOAc
  7. washThe combined organics were washed with saturated NaCl solution
  8. dry with materialdried over a mixture of activated charcoal and Na2SO4
  9. filtrationfiltered through Celite
  10. customevaporated

Sources & evidence

ORD record
ord-9df359626ec84d378fb0fea27980be46
Source dataset
uspto-grants-2010_01
Patent number
US07645775B2

Reaction notes

Loading…