Hexane → HCID 67214738, compound

HRID 2420793Notes

Reaction equation

HRID 2420793 reaction equation
[NH2:1][C:2]1[C:6]([C:7]([O:9][CH2:10][CH3:11])=[O:8])=[CH:5][NH:4][N:3]=1.[C:12]1([CH3:26])[CH:17]=[C:16]([CH3:18])[CH:15]=[C:14]([CH3:19])[C:13]=1[CH:20]=[C:21]([C:24]#[N:25])[C:22]#[N:23].CCCCCC>N1C=CC=CC=1.C(OCC)C.C(OCC)(=O)C>[NH2:25][C:24]1[N:3]2[N:4]=[CH:5][C:6]([C:7]([O:9][CH2:10][CH3:11])=[O:8])=[C:2]2[N:1]=[C:20]([C:13]2[C:12]([CH3:26])=[CH:17][C:16]([CH3:18])=[CH:15][C:14]=2[CH3:19])[C:21]=1[C:22]#[N:23]

Participants

7

Reactant 3

HCID 8058HexaneHCID 5930572-[(2,4,6-Trimethylphenyl)methylene]propanedinitrile2×HCID 178469928HCID 178469928, compound

Product 1

HCID 67214738HCID 67214738, compound

Reagents, catalysts & solvents 3

HCID 1049PyridineSolventHCID 3283Diethyl EtherSolventHCID 8857Ethyl AcetateSolvent

Procedure

In a variation of Example 8, Step A, a solution of 5.69 g (36.7 mmol) of 3-amino-4-carbethoxypyrazole and 6.00 g (30.6 mmol) of (mesitylmethylene)malononitrile (Intermediate 3) in 34 mL of anhydrous pyridine was stirred at reflux under air for 6 days. The dark solution was cooled and concentrated in vacuo. The residue was flash chromatographed on silica gel (gradient elution with 20-50% ethyl acetate in hexane) to give the crude product as a dark solid contaminated with another regioisomer. This material was dissolved in diethyl ether containing a little ethyl acetate. Addition of hexane precipitated a dark, tacky solid. This semisolid was collected and redissolved in 9:1 dichloromethane:methanol. Addition of hexane resulted in precipitation. The precipitate was collected on a filter and dried to give the title compound as a yellow solid. LC-MS 350 (M+1).

Workup

  1. temperatureat reflux under air for 6 days
  2. temperatureThe dark solution was cooled
  3. concentrationconcentrated in vacuo
  4. customchromatographed on silica gel (gradient elution with 20-50% ethyl acetate in hexane)
  5. customto give the crude product as a dark solid
  6. customprecipitated a dark, tacky solid
  7. customThis semisolid was collected
  8. dissolutionredissolved in 9:1 dichloromethane
  9. additionAddition of hexane
  10. customresulted in precipitation
  11. customThe precipitate was collected on
  12. filtrationa filter
  13. customdried

Sources & evidence

ORD record
ord-d9601478a46f40ab9c140c251173aa6b
Source dataset
uspto-grants-2011_06
Patent number
US07956061B2

Reaction notes

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