Sodium Hydroxide → HCID 68754904, compound

HRID 2098208Notes

Reaction equation

HRID 2098208 reaction equation
[N+:1]([C:4]1[S:8][CH:7]=[C:6]([C:9]#[N:10])[C:5]=1[C:11]1[CH:16]=[N:15][CH:14]=[CH:13][N:12]=1)([O-])=O.[Sn](Cl)Cl.[OH-].[Na+]>Cl>[NH2:1][C:4]1[S:8][CH:7]=[C:6]([C:9]#[N:10])[C:5]=1[C:11]1[CH:16]=[N:15][CH:14]=[CH:13][N:12]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 24479Stannous ChlorideHCID 68755976HCID 68755976, compound

Product 1

HCID 68754904HCID 68754904, compoundYield 21.3%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

To 5-nitro-4-(pyrazin-2-yl)thiophene-3-carbonitrile (166 mg, 0.72 mmol) in conc HCl (3 mL) at rt was added tin(II) chloride (327 mg, 1.7 mmol). This was stirred at rt for 2 h, whereupon the reaction mixture was basified with aqueous NaOH and extracted with EtOAc. The combined organic extracts were dried (Na2SO4), filtered and concentrated to give a brown oil (31 mg, 21%). HPLC method [4], retention time=1.458 min; MS (ESI) 203.1 (MH+).

Workup

  1. extractionextracted with EtOAc
  2. dry with materialThe combined organic extracts were dried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-f1d72779281f4873b5265db1b106163e
Source dataset
uspto-grants-2013_05
Patent number
US08450363B2

Reaction notes

Loading…