Methanol → HCID 14450291, compound

HRID 568398Notes

Reaction equation

HRID 568398 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.[H-].C([Al+]CC(C)C)C(C)C.C[OH:32]>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:32]

Participants

6

Reactant 3

HCID 887MethanolHCID 14450289HCID 14450289, compoundHCID 21225700Diisobutylaluminumhydride

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 hydride 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-4c2fa09ceaf34aa7a8ca99ef1f84a79c
Source dataset
uspto-grants-1988_03
Patent number
US04728653

Reaction notes

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