Malononitrile → HCID 86664260, compound

HRID 1518906Notes

Reaction equation

HRID 1518906 reaction equation
[C:1]([NH:11][C:12](=[O:20])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[F:19])(=[O:10])/[CH:2]=[CH:3]/[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[C:21](#[N:25])[CH2:22][C:23]#[N:24]>C1(C)C=CC=CC=1>[C:23]([CH:22]([C:21]#[N:25])[C@@H:3]([C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1)[CH2:2][C:1]([NH:11][C:12](=[O:20])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[F:19])=[O:10])#[N:24]

Participants

4

Reactant 2

HCID 8010MalononitrileHCID 49782231HCID 49782231, compound

Product 1

HCID 86664260HCID 86664260, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

(E)-N-Cinnamoyl-2-fluorobenzamide (26.9 mg, 0.1 mmol), malononitrile (13.2 mg, 0.2 mmol) and the compound (10 mol %) shown in the following Table 2 as an asymmetric catalyst were stirred in toluene (1.0 mL) at room temperature for 27 hr. The reaction mixture was purified by silica gel column chromatography (n-hexane/ethyl acetate=4/1) to give the title compound as a white solid.

Workup

  1. customThe reaction mixture was purified by silica gel column chromatography (n-hexane/ethyl acetate=4/1)

Sources & evidence

ORD record
ord-633cb9935a7b49b986df2d2ff6de3e66
Source dataset
uspto-grants-2015_07
Patent number
US09073823B2

Reaction notes

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