Sodium hydride → HCID 69799897, compound

HRID 1815998Notes

Reaction equation

HRID 1815998 reaction equation
[H-].[Na+].[CH2:3]([O:10][C:11]1[CH:18]=[CH:17][C:14]([CH:15]=O)=[CH:13][CH:12]=1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[C:19]([CH2:21][C:22]1[S:23][CH:24]=[C:25]([C:27]([F:30])([F:29])[F:28])[N:26]=1)#[N:20]>CCO>[CH2:3]([O:10][C:11]1[CH:18]=[CH:17][C:14]([CH:15]=[C:21]([C:22]2[S:23][CH:24]=[C:25]([C:27]([F:30])([F:28])[F:29])[N:26]=2)[C:19]#[N:20])=[CH:13][CH:12]=1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 78109Benzaldehyde, 4-(phenylmethoxy)-HCID 224960522-(4-(Trifluoromethyl)thiazol-2-yl)acetonitrile

Product 1

HCID 69799897HCID 69799897, compoundYield 65.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

NaH (516 mg, 60% dispersion in mineral oil, 12.9 mmole) was reacted with absolute EtOH (10 mL) at 0° C. After gas evolution had ceased the mixture was warmed to RT. 4-Benzyloxybenzaldehyde (2.05 g, 9.68 mmole) was added all at once as a solid. To this mixture was added dropwise a solution of 2-cyanomethyl-4(trifluoromethyl)thiazole (1.24 g) in absolute EtOH (20 mL). The reaction was stirred for 4 hr, then the solid was collected by filtration and washed with hexanes to give the title compound (1.64 g, 42% over 2 steps) as a yellow solid: 1H NMR (300 MHz. CDCl3) δ 8.25 (s, 1 H), 8.00 (d, J=6 Hz, 2 H), 7.79(s, 1 H), 7.40 (m, 5 H), 7.10(d, J=6 Hz, 2 H), 5.18 (s, 2 H).

Workup

  1. filtrationthe solid was collected by filtration
  2. washwashed with hexanes

Sources & evidence

ORD record
ord-bd9c7a4c5c0149b0bc7647c3a7bbe362
Source dataset
uspto-grants-2005_04
Patent number
US06881736B1

Reaction notes

Loading…