Sodium hydride → HCID 22890587, compound
Reaction equation
[NH2:1][CH:2]([CH3:15])[CH2:3][CH2:4][C:5]1[CH:6]=[CH:7][C:8]([CH2:11][CH2:12][CH2:13][NH2:14])=[N:9][CH:10]=1.[H-].[Na+]>>[CH3:15][CH:2]1[NH:1][C:10]2[N:9]=[C:8]([CH2:11][CH2:12][CH2:13][NH2:14])[CH:7]=[CH:6][C:5]=2[CH2:4][CH2:3]1Participants
Conditions
- Temperature
- 100 °C
Procedure
A solution of the diamine 9-3 (1.87 g, 9.05 mmol) in xylenes (100 mL) was degassed with nitrogen gas then treated with NaH (1.3 g, 54.3 mmol) and then heated to 100° C. for 16 hours. Mass spectrum indicated desired product formed. The mixture was cooled, EtOH added then poured into water and extracted with EtOAc. The organic layer was washed with water, brine dried (MgSO4) and concentrated. Purification of the residue on silica gel (2%-5% MeOH/CHCl3) gave a solid which was shown to be the N-acetate of the desired compound by mass spectrum and nm. Treatment with aqueous NaOH/THF/MeOH at reflux for 72 hours then afforded the hydrolysed product. The THF/MeOH was removed in vacuo, the residue was partitioned between water and CH2Cl2, washed with brine and dried over MgSO4. Removal of the solvent afforded the title compound 9-4.
Sources & evidence
- ORD record
- ord-9d458e48c833441890327a436a70c3d5
- Source dataset
- uspto-grants-2002_10
- Patent number
- US06472403B2
Reaction notes
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