Sodium hydride → 1-(2-Methyl-1,3,4-thiadiazol-5-ylmethoxy)-4-[2-methyl-2-(2-pyridinyloxy)ethoxy]benzene

HRID 1588301Notes

Reaction equation

[CH3:1][CH:2]([O:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][N:14]=1)[CH2:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([OH:11])=[CH:7][CH:6]=1.[H-].[Na+].[CH3:21][C:22]1[S:23][C:24]([CH2:27]Cl)=[N:25][N:26]=1>CN(C=O)C>[CH3:21][C:22]1[S:23][C:24]([CH2:27][O:11][C:8]2[CH:7]=[CH:6][C:5]([O:4][CH2:3][CH:2]([CH3:1])[O:12][C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][N:14]=3)=[CH:10][CH:9]=2)=[N:25][N:26]=1

Participants

Conditions

Temperature: 80 °C

Procedure

A solution of 4.46 g (18.2 mmol) of 4-[2-methyl-2-(2-pyridinyloxy)ethoxy]phenol in 30 ml of DMF was added to a suspension of 0.6 g (1.1 eq.) of NaH (80% dispersion in mineral oil) in 30 ml of DMF at RT and the mixture was then heated at 80° C. for 1 h. A solution of 2.7 g (18.2 mmol) of 2-methyl-5-chloromethyl-1,3,4-thiadiazole in 20 ml of DMF was added and the mixture was then heated at 120° C. for 6 h. The solvent was stripped off in a rotary evaporator, the residue was taken up in ethyl acetate, and the solution was washed three times with water. Drying, removal of the solvent and purification of the crude product by chromatography (silica gel, cyclohexane/ethyl acetate 2:1) resulted in 2.9 g (45%) of colorless crystals; melting point 72°-78° C.

Workup

temperaturethe mixture was then heated at 120° C. for 6 h
customThe solvent was stripped off in a rotary evaporator
washthe solution was washed three times with water
customDrying
customremoval of the solvent and purification of the crude product by chromatography (silica gel, cyclohexane/ethyl acetate 2:1)

Sources & evidence

ORD record: ord-1533e62508c842118e907ce869bb0079
Source dataset: uspto-grants-1993_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05221684

Reaction notes

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