Sodium hydride → 3-(5-(Benzylthio)-1,3,4-thiadiazol-2-ylthio)pyrazine-2-carbonitrile

HRID 1968397Notes

Reaction equation

[CH2:1]([S:8][C:9]1[S:13][C:12]([SH:14])=[N:11][N:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].Cl[C:18]1[C:19]([C:24]#[N:25])=[N:20][CH:21]=[CH:22][N:23]=1>CN(C=O)C.C1C=CC=CC=1>[CH2:1]([S:8][C:9]1[S:13][C:12]([S:14][C:18]2[C:19]([C:24]#[N:25])=[N:20][CH:21]=[CH:22][N:23]=2)=[N:11][N:10]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of 5-(benzylthio)-1,3,4-thiadiazole-2-thiol (240 mg, 1.00 mmol) in DMF and benzene (4 ml, 1/1) was added NaH (60% dispersion in mineral oil, 44 mg, 1.10 mmol) slowly at 0° C. under a nitrogen atmosphere. The resulting suspension was stirred at 0° C. for 15 minutes and then to the mixture was added 3-chloropyrazine-2-carbonitrile (140 mg, 1.00 mmol). The reaction was stirred at room temperature for 2 hr. The reaction was quenched with saturated NH4Cl solution and extracted with EtOAc. The combined organic layers were washed with water, brine and dried over MgSO4. Removal of the solvent gave the crude product which was purified by chromatography to give the title compound as off-white solid.

Workup

stirringThe reaction was stirred at room temperature for 2 hr
customThe reaction was quenched with saturated NH4Cl solution
extractionextracted with EtOAc
washThe combined organic layers were washed with water, brine
dry with materialdried over MgSO4
customRemoval of the solvent
customgave the crude product which
customwas purified by chromatography

Sources & evidence

ORD record: ord-71d0f492365746c9b33e3bd83d4faf7b
Source dataset: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08426358B2

Reaction notes

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