2-Ethylhexanoic Acid → HCID 178441466, compound

HRID 1655477Notes

Reaction equation

HRID 1655477 reaction equation
[CH2:1]([C:5]1[N:9]([CH2:10][C:11]2[CH:16]=[CH:15][C:14]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=3[C:23]#[N:24])=[CH:13][CH:12]=2)[C:8]2[C:25]([CH2:29][O:30][CH3:31])=[CH:26][CH:27]=[CH:28][C:7]=2[N:6]=1)[CH2:2][CH2:3][CH3:4].C[Sn]([N:36]=[N+:37]=[N-:38])(C)C.[Na:39].C(C(CCCC)C(O)=O)C>C1(C)C=CC=CC=1.C(OCC)(=O)C.CO>[Na:39].[CH2:1]([C:5]1[N:9]([CH2:10][C:11]2[CH:12]=[CH:13][C:14]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=3[C:23]3[NH:38][N:37]=[N:36][N:24]=3)=[CH:15][CH:16]=2)[C:8]2[C:25]([CH2:29][O:30][CH3:31])=[CH:26][CH:27]=[CH:28][C:7]=2[N:6]=1)[CH2:2][CH2:3][CH3:4]

Participants

8

Reactant 4

HCID 86972-Ethylhexanoic AcidHCID 5104973Azido(trimethyl)stannaneHCID 5360545SodiumHCID 19792117HCID 19792117, compound

Product 1

HCID 178441466HCID 178441466, compoundYield 31%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 1140TolueneSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 2-butyl-1-[(2'-cyanobiphenyl-4-yl)methyl]- 7-methoxymethylbenzimidazole (0.6 g) and trimethyltin azide (1.2 g) in toluene (12 ml) was heated for 3 days under reflux in toluene (12 ml). The solvent was distilled off. To the residue was added 1N-HCl (8 ml) and the mixture was stirred for a while, followed by extraction with ethyl acetate. The organic layer was washed with water and dried, then the solvent was distilled off. The residue was purified by column chromatography on silica gel to give an oil. The product was dissolved in ethyl acetate, to which was added a methanol solution of sodium salt of 2-ethyl hexanoic acid (0.25 g). The mixture was concentrated. Crystals separated out were recrystallized from toluene --ethyl acetate to afford colorless crystals (0.22 g, 31%), m.p.175-178° C.

Workup

  1. temperaturewas heated for 3 days
  2. distillationThe solvent was distilled off
  3. additionTo the residue was added 1N-HCl (8 ml)
  4. extractionfollowed by extraction with ethyl acetate
  5. washThe organic layer was washed with water
  6. customdried
  7. distillationthe solvent was distilled off
  8. customThe residue was purified by column chromatography on silica gel
  9. customto give an oil
  10. concentrationThe mixture was concentrated
  11. customCrystals separated out
  12. customwere recrystallized from toluene

Sources & evidence

ORD record
ord-3d798e8655b04152a12624ea521ecca2
Source dataset
uspto-grants-1993_10
Patent number
US05250554

Reaction notes

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