2-[(2,4,6-Trimethylphenyl)methylene]propanedinitrile → HCID 67214165, compound

HRID 2420794Notes

Reaction equation

HRID 2420794 reaction equation
[NH:1]1[C:5]2[CH2:6][S:7][CH2:8][C:4]=2[C:3]([NH2:9])=[N:2]1.[C:10]1([CH3:24])[CH:15]=[C:14]([CH3:16])[CH:13]=[C:12]([CH3:17])[C:11]=1[CH:18]=[C:19]([C:22]#[N:23])[C:20]#[N:21]>N1C=CC=CC=1>[NH2:23][C:22]1[N:2]2[N:1]=[C:5]3[CH2:6][S:7][CH2:8][C:4]3=[C:3]2[N:9]=[C:18]([C:11]2[C:10]([CH3:24])=[CH:15][C:14]([CH3:16])=[CH:13][C:12]=2[CH3:17])[C:19]=1[C:20]#[N:21]

Participants

4

Reactant 2

HCID 5930572-[(2,4,6-Trimethylphenyl)methylene]propanedinitrile2×HCID 33777858HCID 33777858, compound2×

Product 1

HCID 67214165HCID 67214165, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution of 284 mg (2.01 mmol) of 4,6-dihydro-1H-thieno[3,4-c]pyrazol-3-amine (Intermediate 21) and 395 mg (2.01 mmol) of (mesitylmethylene)malononitrile (Intermediate 3) in 5 mL of anhydrous pyridine was stirred at reflux under air overnight (protected from moisture with a calcium sulfate drying tube) and then cooled and concentrated in vacuo. The residue was stirred with 20 mL of methanol and filtered to remove some insoluble material, which was washed with an additional 5 mL of methanol. The combined filtrate and washings were concentrated. Purification of the residue by flash chromatography on silica gel (gradient elution with 5-15% ethyl acetate in hexane) afforded the title compound as a solid. LC-MS 336 (M+1).

Workup

  1. temperatureat reflux under air overnight (protected from moisture with a calcium sulfate drying tube)
  2. temperaturecooled
  3. concentrationconcentrated in vacuo
  4. filtrationfiltered
  5. customto remove some insoluble material, which
  6. washwas washed with an additional 5 mL of methanol
  7. concentrationThe combined filtrate and washings were concentrated
  8. customPurification of the residue by flash chromatography on silica gel (gradient elution with 5-15% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-a51459df63c345b89d2f493e1d48b7a3
Source dataset
uspto-grants-2011_06
Patent number
US07956061B2

Reaction notes

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