Sodium hydride → HCID 67180494, compound

HRID 2400215Notes

Reaction equation

HRID 2400215 reaction equation
[H-].[Na+].[OH:3][CH2:4][C:5]1[C:6](=[O:11])[NH:7][CH:8]=[CH:9][CH:10]=1.[C:12]([C:14]1[CH:22]=[CH:21][C:17]([C:18](Cl)=[O:19])=[CH:16][CH:15]=1)#[N:13]>C1COCC1>[C:12]([C:14]1[CH:22]=[CH:21][C:17]([C:18]([O:3][CH2:4][C:5]2[C:6](=[O:11])[NH:7][CH:8]=[CH:9][CH:10]=2)=[O:19])=[CH:16][CH:15]=1)#[N:13]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 801724-Cyanobenzoyl chlorideHCID 106304823-(Hydroxymethyl)pyridin-2(1H)-one

Product 1

HCID 67180494HCID 67180494, compoundYield 28.54%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In Example 3, 0.0723 g of 60% NaH was dispersed in mineral oil (0.64 mmol) and was suspended in 50 mL of THF in a 100 mL RBF under the presence of argon gas. Then, 0.2026 g (1.62 mmol) of 3-(hydroxymethyl)pyridine-2(1H)-one was slowly added into the solution. This solution was stirred for 30 min with gentle heating before 0.2661 g (1.61 mmol) of 4-cyanobenzoyl chloride was added. The reaction was stirred with gentle heating for 48 hours. The reaction was quenched with 20 mL of and was washed with ethyl acetate (4×20 mL) and the organic layers combined. The organic layer was washed with brine (3×20 mL) before being dried of MgSO4. The solvent was evaporated in vacuo to produce a white solid. The product was purified with silica gel column chromatography using 10% methanol in dichloromethane as eluent. The yield of the reaction was 0.1175 g (28.54% yield). MP: 200-203° C. IR (cm−1): 3406.04 (m, broad), υ (O—H), 3113.07 (m, broad), υ (N—H), 1728.71 (m), υ (C═O), 1617.96 (s), υ (C═C aromatic). 1H NMR (DMSO-d6, 500 MHz) δ: 5.17 (s, 2H), 6.23 (t, J=6.6 Hz, 1H), 7.42 (dd, J=4.5, 2.0 Hz, 1H), 7.63 (dd, J=4.7, 1.1 Hz, 1H), 8.02 (d, J=4.8, 2H), 8.10 (d, J=4.7, 2H), 11.80 (s, 1H).

Workup

  1. additionwas added
  2. stirringThe reaction was stirred
  3. temperaturewith gentle heating for 48 hours
  4. customThe reaction was quenched with 20 mL of and
  5. washwas washed with ethyl acetate (4×20 mL)
  6. washThe organic layer was washed with brine (3×20 mL)
  7. dry with materialbefore being dried of MgSO4
  8. customThe solvent was evaporated in vacuo
  9. customto produce a white solid
  10. customThe product was purified with silica gel column chromatography

Sources & evidence

ORD record
ord-14cc74e07f2642dd937b815abe0c9ac5
Source dataset
uspto-grants-2014_08
Patent number
US08795630B2

Reaction notes

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