Water → HCID 9885921, compound

HRID 2105256Notes

Reaction equation

HRID 2105256 reaction equation
[N:1]1([CH:6]([C:10]2[CH:15]=[CH:14][C:13]([NH:16][C:17](=[O:30])/[C:18](=[CH:20]/[C:21]3[CH:26]=[CH:25][C:24]([N+:27]([O-])=O)=[CH:23][CH:22]=3)/[CH3:19])=[CH:12][CH:11]=2)[CH:7]([CH3:9])[CH3:8])[CH:5]=[CH:4][N:3]=[CH:2]1.O.[OH-].[Na+]>C1COCC1>[NH2:27][C:24]1[CH:25]=[CH:26][C:21](/[CH:20]=[C:18](\[CH3:19])/[C:17]([NH:16][C:13]2[CH:14]=[CH:15][C:10]([CH:6]([N:1]3[CH:5]=[CH:4][N:3]=[CH:2]3)[CH:7]([CH3:8])[CH3:9])=[CH:11][CH:12]=2)=[O:30])=[CH:22][CH:23]=1

Participants

5

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 22335522HCID 22335522, compound

Product 1

HCID 9885921HCID 9885921, compoundYield 54%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

A mixture of (±)-(E)-N-[4-[1-(1H-imidazol-1-yl)-2-methylpropyl]phenyl]-2-[(4-nitrophenyl)-methylene]propanamide (0.00742 mol) in THF (80 ml) and TiCl3 (30 ml) was stirred at 0° C. for 15 minutes. The mixture was poured into water, ice and NaOH 3N and extracted with CH2Cl2 (2×100 ml). The combined organic layers were dried, filtered and the solvent evaporated. The residue was taken up in CH2Cl2 and (C2H5)2O. The precipitate was filtered off and stirred K2CO3 10% and CH2Cl2, dried, filtered off and evaporated. The residue was crystallized from 2-propanone. The precipitate was filtered off, taken up in Na2CO3 10% and CH2Cl2. The organic layer was dried, filtered off and evaporated. The residue was purified by column chromatography over silica gel (eluent: CH2Cl2/CH3OH/NH4OH 96/4/0.1). The pure fractions were collected and evaporated. The residue was crystallized from (C2H5)2O, yielding 1.5 g (±)-(E)-2-[(4-aminophenyl)methylene]-N-[4-[1-(1H-imidazol-1-yl)-2-methylpropyl]phenyl]propanamide (compound 611).

Workup

  1. extractionextracted with CH2Cl2 (2×100 ml)
  2. customThe combined organic layers were dried
  3. filtrationfiltered
  4. customthe solvent evaporated
  5. filtrationThe precipitate was filtered off
  6. stirringstirred K2CO3 10% and CH2Cl2
  7. customdried
  8. filtrationfiltered off
  9. customevaporated
  10. customThe residue was crystallized from 2-propanone
  11. filtrationThe precipitate was filtered off
  12. customThe organic layer was dried
  13. filtrationfiltered off
  14. customevaporated
  15. customThe residue was purified by column chromatography over silica gel (eluent: CH2Cl2/CH3OH/NH4OH 96/4/0.1)
  16. customThe pure fractions were collected
  17. customevaporated
  18. customThe residue was crystallized from (C2H5)2O

Sources & evidence

ORD record
ord-4a274d948a384941b3cbf8fcd42b1472
Source dataset
uspto-grants-2009_08
Patent number
US07579352B2

Reaction notes

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