Methanol → HCID 54337598, compound

HRID 582017Notes

Reaction equation

HRID 582017 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].C(=O)([O-])[O-].[Na+].[Na+].FC(F)(F)C([O-])=O.[OH:30][CH2:31][CH2:32][CH2:33][NH2+:34][NH2:35].CO>C(Cl)Cl>[NH2:2][C:1]1[N:34]([CH2:33][CH2:32][CH2:31][OH:30])[N:35]=[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

6

Reactant 4

HCID 887MethanolHCID 10340Sodium CarbonateHCID 542422372-Cyano-3-methylthio-3-(4-tolyl)acrylamide2×HCID 86754230HCID 86754230, compound

Product 1

HCID 54337598HCID 54337598, compoundYield 43.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The title compound was prepared from 2-cyano-3-methylthio-3-(4-tolyl)acrylamide (464 mg, 2.0 mmol), sodium carbonate (424 mg, 4.0 mmol) and 1-(3-hydroxypropyl)hydrazinium trifluoroacetate (449 mg, 2.2 mmol) following the procedure used for the compound of Example 12. The crude product was subjected to column chromatography (SiO2, 8% methanol in CH2Cl2) and was recrystallised from ethyl acetate to give the title compound as white crystals (240 mg) m.p. 164-165°. δH (CDCl3) 7.43 (2H, d, J 8.1 Hz), 7.26 (2H, d, J 7.8 Hz), 5.73 (2H, br s), 5.18 (2H, br s), 4.12 (2H, t, J 6.1 Hz), 3.66 (2H, t, J 5.5 Hz), 2.40 (3H, s), 2.04 (2H, quintet, J 6.1 Hz) and 1.59 (1H, br s).

Workup

  1. customwas recrystallised from ethyl acetate

Sources & evidence

ORD record
ord-d93e30943e054ad7baebe2eede6ee637
Source dataset
uspto-grants-1999_07
Patent number
US05922741

Reaction notes

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