Malononitrile → HCID 86588472, compound

HRID 1768430Notes

Reaction equation

HRID 1768430 reaction equation
[NH:1]=[C:2]1[C:11]([C:12]#[N:13])=[C:10]([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([O:20][CH3:21])[CH:15]=2)[C:9]2[C:4](=[CH:5][C:6]([O:22][CH3:23])=[CH:7][CH:8]=2)[S:3]1.SC1C=C(OC)C=CC=1C(C1C=CC=C(OC)C=1)=O.C(#N)C[C:45]#[N:46].N1CCCCC1>C(O)C>[NH:1]=[C:2]1[C:11]([C:45]#[N:46])([C:12]#[N:13])[CH:10]([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([O:20][CH3:21])[CH:15]=2)[C:9]2[C:4](=[CH:5][C:6]([O:22][CH3:23])=[CH:7][CH:8]=2)[S:3]1

Participants

6

Reactant 4

HCID 8010MalononitrileHCID 8082PiperidineHCID 9880202HCID 9880202, compoundHCID 22136817HCID 22136817, compound

Product 1

HCID 86588472HCID 86588472, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2-Imino-3-cyano-7-methoxy-4-(3-methoxy-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 approximately 200 μL of dry ethanol was added piperidine (7.0 μL, 0.06 mmol) at approximately 0° C. The resultant mixture was stirred at approximately 0° C. for approximately 2.5 h. The solvent was evaporated and the residue was purified by flash chromatography (silica gel, EtOAc:hexanes, 1:4) to yield 31 mg (75%) of 2-imino-3-cyano-7-methoxy-4-(3′-methoxy-phenyl)-2H-thiochromene-3-carbonitrile 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 (bs, 1H), 6.68 (dd, J=9.1, 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 (silica gel, EtOAc:hexanes, 1:4)

Sources & evidence

ORD record
ord-ae2510af856e492e84ec614fe583aa14
Source dataset
uspto-grants-2007_06
Patent number
US07235674B2

Reaction notes

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