Sodium Hydroxide → HCID 53789590, compound

HRID 582015Notes

Reaction equation

[C:1]([C:3](=[C:7](SC)[C:8]1[CH:13]=[CH:12][C:11]([CH3:14])=[CH:10][CH:9]=1)[C:4]([NH2:6])=[O:5])#[N:2].Cl.[N+:18]([C:21]1[CH:22]=[C:23]([NH:27][NH2:28])[CH:24]=[CH:25][CH:26]=1)([O-:20])=[O:19].[OH-].[Na+]>>[NH2:2][C:1]1[N:27]([C:23]2[CH:24]=[CH:25][CH:26]=[C:21]([N+:18]([O-:20])=[O:19])[CH:22]=2)[N:28]=[C:7]([C:8]2[CH:13]=[CH:12][C:11]([CH3:14])=[CH:10][CH:9]=2)[C:3]=1[C:4]([NH2:6])=[O:5]

Participants

Reactant 3

HCID 14798Sodium Hydroxide

HCID 54642853-Nitrophenylhydrazinium(1+) chloride

HCID 542422372-Cyano-3-methylthio-3-(4-tolyl)acrylamide2×

Product 1

HCID 53789590HCID 53789590, compoundYield 7.4%

Procedure

The title compound was prepared from 2-cyano-3-methylthio-3-(4-tolyl)acrylamide (464 mg, 2.0 mmol), 3-nitrophenylhydrazine hydrochloride (417 mg, 2.2 mmol) and sodium hydroxide (88 mg, 2.2 mmol) following the procedure used for the compound of Example 12. The crude product was purified by column chromatography (SiO2, 50% ethyl acetate in hexane) and recrystallisation from ethyl acetate to give the title compound as white crystals (50 mg) m.p. 237-238°. δH (d6DMSO) 8.42 (1H, s), 8.21 (1H, d, J 7.8 Hz), 8.11 (1H, d, J 7.8 Hz), 7.79 (1H, t, J 8.2 Hz), 7.50 (2H, d, J 8.0 Hz), 7.30 (2H, d, J 8.1 Hz), 6.70 (2H, s), 5.50 (2H, br s) and 2.37 (3H, s).

Workup

customThe crude product was purified by column chromatography (SiO2, 50% ethyl acetate in hexane) and recrystallisation from ethyl acetate

Sources & evidence

ORD record: ord-af20d5478a954ad2a721b70936e6fa62
Source dataset: uspto-grants-1999_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05922741

Reaction notes

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