Methanol → HCID 14450291, compound

HRID 1199543Notes

Reaction equation

HRID 1199543 reaction equation
[NH2:1][C:2]1[C:7]([C:8]([F:11])([F:10])[F:9])=[CH:6][C:5]([N:12]2[CH:16]=[C:15]([CH3:17])[N:14]=[C:13]2[CH3:18])=[CH:4][C:3]=1[C:19]#N.C([Al]CC(C)C)C(C)C.C[OH:31]>O1CCCC1.C1(C)C=CC=CC=1>[NH2:1][C:2]1[C:7]([C:8]([F:11])([F:10])[F:9])=[CH:6][C:5]([N:12]2[CH:16]=[C:15]([CH3:17])[N:14]=[C:13]2[CH3:18])=[CH:4][C:3]=1[CH:19]=[O:31]

Participants

6

Reactant 3

HCID 887MethanolHCID 14450289HCID 14450289, compoundHCID 16682954Dibah

Product 1

HCID 14450291HCID 14450291, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent

Procedure

To an ice-cooled stirred solution of 1-(4-amino-3-cyano-5-trifluoromethylphenyl)-2,4-dimethylimidazole (0.7 g) in tetrahydrofuran (10 cm3) was added 3.5 cm3 of a 1.5M solution of diisobutyl aluminium in toluene. The mixture was heated at 40° for 2 hours, cooled in ice, treated with methanol (2 cm3), and evaporated in vacuo. The residue was treated with water (25 cm3) and 2M hydrochloric acid (5 cm3), and heated on a steam bath for five minutes. The solution was then cooled, basified to pH 8 with aqueous sodium carbonate solution, and extracted with chloroform:methanol, 20:1 (3×30 cm3). The combined organic extracts were dried (MgSO4), evaporated in vacuo, and the residue was chromatographed on silica (Merck "MK 60.9385" [Trade Mark]) eluting with ethyl acetate:methanol, 50:1, to afford 1-(4-amino-3-formyl-5-trifluoromethylphenyl)-2,4-dimethylimidazole, m.p. 200°-202°, (0.391 g).

Workup

  1. temperatureThe mixture was heated at 40° for 2 hours
  2. temperaturecooled in ice
  3. customevaporated in vacuo
  4. additionThe residue was treated with water (25 cm3) and 2M hydrochloric acid (5 cm3)
  5. temperatureheated on a steam bath for five minutes
  6. temperatureThe solution was then cooled
  7. extractionextracted with chloroform
  8. dry with materialThe combined organic extracts were dried (MgSO4)
  9. customevaporated in vacuo
  10. customthe residue was chromatographed on silica (Merck "MK 60.9385" [Trade Mark])
  11. washeluting with ethyl acetate

Sources & evidence

ORD record
ord-c7e3450734934f2cbf297ce6e35225ee
Source dataset
uspto-grants-1990_02
Patent number
US04900839

Reaction notes

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