Sodium methanethiolate → (E)-4-[2-[2-[[(p-Hydroxyphenyl)sulfonyl]amino]phenyl]ethenyl]pyridine

HRID 1741018Notes

Reaction equation

C[O:2][C:3]1[CH:8]=[CH:7][C:6]([S:9]([NH:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2/[CH:19]=[CH:20]/[C:21]2[CH:26]=[CH:25][N:24]=[CH:23][CH:22]=2)(=[O:11])=[O:10])=[CH:5][CH:4]=1.C[S-].[Na+]>CN(C=O)C>[OH:2][C:3]1[CH:4]=[CH:5][C:6]([S:9]([NH:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2/[CH:19]=[CH:20]/[C:21]2[CH:22]=[CH:23][N:24]=[CH:25][CH:26]=2)(=[O:11])=[O:10])=[CH:7][CH:8]=1

Participants

Conditions

Temperature: 100 °C

Procedure

In DMF was dissolved 2.00 g of the (E)-4-[2-[2-[[(p-methoxyphenyl)sulfonyl]amino]phenyl]ethenyl]pyridine obtained in Example 3, followed by addition of 1.91 g of sodium methanethiolate, and the mixture was stirred at 100° C. overnight and then after-treated. The resulting crystals were recrystallized from methanol to provide 0.19 g of the title compound (white powders).

Workup

additionafter-treated
customThe resulting crystals were recrystallized from methanol

Sources & evidence

ORD record: ord-7b3a3dcd242e450f92af971fb91c5a74
Source dataset: uspto-grants-1999_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05972976

Reaction notes

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