Trimethyl orthoformate → 2-((1-benzyl-1H-pyrazol-4-yl)(methoxy)methylene)malononitrile

HRID 64303Notes

Reaction equation

HRID 64303 reaction equation
[CH2:1]([N:8]1[CH:12]=[C:11]([C:13]([OH:19])=[C:14]([C:17]#[N:18])[C:15]#[N:16])[CH:10]=[N:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH:20](OC)(OC)OC>>[CH2:1]([N:8]1[CH:12]=[C:11]([C:13]([O:19][CH3:20])=[C:14]([C:15]#[N:16])[C:17]#[N:18])[CH:10]=[N:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 9005Trimethyl orthoformateHCID 1176683522-((1-Benzyl-1H-pyrazol-4-yl)(hydroxy)methylene)malononitrile

Product 1

HCID 1176680512-((1-benzyl-1H-pyrazol-4-yl)(methoxy)methylene)malononitrileYield 51.8%

Procedure

A solution of 2-((1-benzyl-1H-pyrazol-4-yl)(hydroxy)methylene)malononitrile (26.5 g, 106 mmol) in CH(OMe)3 (250 mL) was heated to 75° C. for 16 hr. Then the solution was concentrated. The residue was washed with MeOH (50 mL) to give 14.5 g (51.8%) of 2-((1-benzyl-1H-pyrazol-4-yl)(methoxy)methylene)malononitrile as an off-white solid. 1H NMR (DMSO-d6) δ 8.71 (s, 1H), 8.08 (s, 1H), 7.42-7.24 (m, 5H), 5.46 (s, 2H), 4.12 (s, 3H). MS (ESI) m/e [M+1]+ 264.9.

Workup

  1. concentrationThen the solution was concentrated
  2. washThe residue was washed with MeOH (50 mL)

Sources & evidence

ORD record
ord-aa72221a92b14bb09df7e7b47b44f883
Source dataset
uspto-grants-2016_09
Patent number
US09447106B2

Reaction notes

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