Sodium Chloride → HCID 11321832, compound

HRID 1175182Notes

Reaction equation

HRID 1175182 reaction equation
BrBr.[CH3:3][O:4][C:5]([N:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH2:8]1)=[O:6].[NH2:13][C:14]([NH2:16])=[S:15].[Na+].[Cl-]>CN(C=O)C.CC#N>[CH3:3][O:4][C:5]([N:7]1[CH2:8][CH:9]=[CH:10][C@H:11]2[S:15][C:14]([NH2:16])=[N:13][C@@H:12]12)=[O:6]

Participants

7

Reactant 4

HCID 5234Sodium ChlorideHCID 24408Bromine2×HCID 2723790ThioureaHCID 11007981Methyl pyridine-1(2H)-carboxylate

Product 1

HCID 11321832HCID 11321832, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent2×HCID 6342AcetonitrileSolvent

Procedure

A solution of Br2 (0.71 ml, 13.9 mmol, 1 equiv.) in DMF (5 ml) is added over 10 min to a solution of N-methoxycarbonyl-1,2-dihydropyridine 1 (1.92 g, 13 mmol, 1 equiv.) and of thiourea (3.95 g, 52 mmol, 4 equiv.) in DMF (15 ml)/CH3CN (5 ml) at ambient temperature and under argon. The reaction being complete from the end of the addition of the bromine, the reaction mixture is concentrated approximately twofold, poured onto ice-cold water (200 ml) and then filtered through a Buchner funnel. The filtrate is basified (5% Na2CO3) until a pH of greater than 10 is obtained and is then saturated with NaCl. After extracting with DCM, drying over MgSO4 and evaporating the solvent, the liquid obtained (10.8 g) is chromatographed on silica gel using DCM (sat. NH3) and then DCM (sat. NH3)/MeOH, 2%. The product 6 (Rf=0.39, DCM/MeOH(NH3), 98:2) is obtained in the form of a white solid (0.32 g, 11%).

Workup

  1. concentrationthe reaction mixture is concentrated approximately twofold
  2. additionpoured onto ice-cold water (200 ml)
  3. filtrationfiltered through a Buchner funnel
  4. customis obtained
  5. extractionAfter extracting with DCM
  6. dry with materialdrying over MgSO4
  7. customevaporating the solvent
  8. customthe liquid obtained (10.8 g)
  9. customis chromatographed on silica gel

Sources & evidence

ORD record
ord-c82eb34f867a45f085b7fb7030efd8ef
Source dataset
uspto-grants-2010_11
Patent number
US07838681B2

Reaction notes

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