Citric Acid → HCID 86596504, compound

HRID 1373108Notes

Reaction equation

HRID 1373108 reaction equation
Cl[C:2]1[CH:7]=[C:6](C(OC(C)(C)C)=O)[CH:5]=[C:4]([O:15][CH3:16])[N:3]=1.[CH3:17][S-:18].[Na+].C(O)(=O)[CH2:21][C:22]([CH2:27]C(O)=O)([C:24](O)=O)[OH:23].[CH3:33]N(C=O)C>>[CH3:16][O:15][C:4]1[N:3]=[C:2]([CH3:33])[CH:7]=[C:6]([C:17]([O:23][C:22]([CH3:27])([CH3:24])[CH3:21])=[S:18])[CH:5]=1

Participants

5

Reactant 4

HCID 311Citric AcidHCID 6228DimethylformamideHCID 4378561Sodium methanethiolateHCID 22253007HCID 22253007, compound

Product 1

HCID 86596504HCID 86596504, compound

Procedure

t-Butyl 2-chloro-6-methoxypyridine-4-carboxylate (D20) (0.72 g) was heated with sodium methanethiolate (0.414 g) in DMF (12 ml) at 60° C. for 50 min. The solution was poured into 10% aq. citric acid and extracted twice with ethyl acetate. The combined extracts were washed with aqueous sodium bicarbonate, water and brine, dried (MgSO4) and evaporated to a yellow semi-solid which was chromatographed on silica, eluting with hexane/ethyl acetate, giving D21 (0.33 g).

Workup

  1. extractionextracted twice with ethyl acetate
  2. washThe combined extracts were washed with aqueous sodium bicarbonate, water and brine
  3. dry with materialdried (MgSO4)
  4. customevaporated to a yellow semi-solid which
  5. customwas chromatographed on silica
  6. washeluting with hexane/ethyl acetate
  7. customgiving D21 (0.33 g)

Sources & evidence

ORD record
ord-02929531f68a45efbcfcb5bcccb985e0
Source dataset
uspto-grants-2007_01
Patent number
US07160905B2

Reaction notes

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