Malononitrile → HCID 9880202, compound

HRID 1826987Notes

Reaction equation

HRID 1826987 reaction equation
[SH:1][C:2]1[CH:7]=[C:6]([O:8][CH3:9])[CH:5]=[CH:4][C:3]=1[C:10]([C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([O:18][CH3:19])[CH:13]=1)=O.[C:20](#[N:24])[CH2:21][C:22]#[N:23].N1CCCCC1>C(O)C>[NH:24]=[C:20]1[C:21]([C:22]#[N:23])=[C:10]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([O:18][CH3:19])[CH:13]=2)[C:3]2[C:2](=[CH:7][C:6]([O:8][CH3:9])=[CH:5][CH:4]=2)[S:1]1

Participants

5

Reactant 3

HCID 8010MalononitrileHCID 8082PiperidineHCID 22136817HCID 22136817, compound

Product 1

HCID 9880202HCID 9880202, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2-Imino-3-cyano-7-methoxy-4-(3′-phenyl)-2H-thiochromene: To a mixture of (2-mercapto-4-methoxyphenyl)-(3′-methoxyphenyl)-methanone (35 mg, 0.13 mmol) and malononitrile (8.5 mg, 0.13 mmol) in 200 μL of dry ethanol was added piperidine (7.0 μL, 0.06 mmol) at 0° C. The resultant mixture was stirred at 0° C. for 2.5 h. The solvent was evaporated and the residue was purified by flash chromatography (25% ethyl acetate/hexanes) to yield 31 mg (75%) of 2-imino-3-cyano-7-methoxy-4-(3′-methoxy-phenyl)-2H-thiochromene as an orange waxy oil. 1H NMR (CDCl3): 9.31 (brs, 1H), 7.42–7.46 (m, 1H), 7.03–7.11 (m, 2H), 6.91 (d, J=7.8 Hz, 1H), 6.85–6.86 (m, 1H), 6.80 (brs, 1H), 6.68 (dd, J=9.1 and 2.6 Hz, 1H), 3.85 (s, 3H), 3.84 (s, 3H).

Workup

  1. customThe solvent was evaporated
  2. customthe residue was purified by flash chromatography (25% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-682b238282014178b1f2fe209b80a6f4
Source dataset
uspto-grants-2006_05
Patent number
US07053117B2

Reaction notes

Loading…