Sodium hydride → HCID 178467941, compound

HRID 1721992Notes

Reaction equation

HRID 1721992 reaction equation
[H-].[Na+].[OH:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[NH:11][CH:12]=[C:13]([C:15]3[S:16][CH:17]=[CH:18][CH:19]=3)[N:14]=2)=[CH:6][CH:5]=1.S(C1C=CC(C)=CC=1)([O-])(=O)=O.C1(C2[N:41]([CH2:42][CH2:43][O:44][CH2:45][CH3:46])[CH2:40][CH:39]([CH2:47]O)[O:38]2)C=CC=CC=1>CN(C=O)C.O>[NH3:11].[CH2:45]([O:44][CH2:43][CH2:42][NH:41][CH2:40][CH:39]([OH:38])[CH2:47][O:3][C:4]1[CH:5]=[CH:6][C:7]([C:10]2[NH:11][CH:12]=[C:13]([C:15]3[S:16][CH:17]=[CH:18][CH:19]=3)[N:14]=2)=[CH:8][CH:9]=1)[CH3:46]

Participants

8

Reactant 4

HCID 24758Sodium hydrideHCID 85570p-ToluenesulfonateHCID 13798876HCID 13798876, compoundHCID 178515900HCID 178515900, compound

Product 2

HCID 222AmmoniaHCID 178467941HCID 178467941, compoundYield 13.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent3×

Conditions

Temperature
70 °C

Procedure

Under N2, NaH (60% oil dispersion, 1 g, 0.025 mol) was added to DMF (20 ml) and heated at 70° C. while a solution of 2-(4-hydroxyphenyl)-4-(2-thienyl)imidazole (5.0 g, 0.021 mol) in DMF (40 ml) was added dropwise. After heating at 70° C. for 0.5 hours, a solution of the tosylate of 2 (0.022 mol) in DMF (25 ml) was added dropwise and the mixture heated at 110° C. After 18 hours, the reaction mixture was poured into H2O and the suspension extracted with EtOAc (4X). The organic extracts were washed with H2O, saturated NaCl, dried, filtered and concentrated to dryness. The residue was treated with AcOH (25 ml) and H2O (175 ml) and the mixture stirred at room temperature. After 18 hours, the aqueous layer was extracted with Et2O (2X), adjusted to ph>10 with saturated Na2CO3 and extracted with CHCl3 (3X). The CHCl3 extracts were dried, filtered and concentrated to dryness. The residue was chromatographed on silica gel eluting with 5% CH3OH--CHCl3 saturated with NH3 to yield 0.56 g (6.6%) of 3; m.p. 144°-6° C. (CH3CN).

Workup

  1. additionwas added dropwise
  2. temperaturethe mixture heated at 110° C
  3. extractionthe suspension extracted with EtOAc (4X)
  4. washThe organic extracts were washed with H2O, saturated NaCl
  5. customdried
  6. filtrationfiltered
  7. concentrationconcentrated to dryness
  8. additionThe residue was treated with AcOH (25 ml) and H2O (175 ml)
  9. waitAfter 18 hours
  10. extractionthe aqueous layer was extracted with Et2O (2X)
  11. extractionextracted with CHCl3 (3X)
  12. dry with materialThe CHCl3 extracts were dried
  13. filtrationfiltered
  14. concentrationconcentrated to dryness
  15. customThe residue was chromatographed on silica gel eluting with 5% CH3OH

Sources & evidence

ORD record
ord-ce0168112d1e4849855483dd8ff48193
Source dataset
uspto-grants-1989_08
Patent number
US04853383

Reaction notes

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