Sodium Carbonate → HCID 54502946, compound

HRID 1740116Notes

Reaction equation

HRID 1740116 reaction equation
[CH2:1]([O:3][C:4](=[O:15])[C:5]([C:11](=O)[CH2:12][CH3:13])=[C:6]([S:9][CH3:10])SC)[CH3:2].Cl.[Br:17][C:18]1[CH:23]=[C:22]([CH3:24])[C:21]([NH:25][NH2:26])=[C:20]([CH3:27])[CH:19]=1.C(=O)([O-])[O-].[Na+].[Na+]>C(O)C>[CH2:1]([O:3][C:4]([C:5]1[C:11]([CH2:12][CH3:13])=[N:26][N:25]([C:21]2[C:20]([CH3:27])=[CH:19][C:18]([Br:17])=[CH:23][C:22]=2[CH3:24])[C:6]=1[S:9][CH3:10])=[O:15])[CH3:2]

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 21837319(4-bromo-2,6-dimethylphenyl)hydrazinehydrochlorideHCID 53844191HCID 53844191, compound

Product 1

HCID 54502946HCID 54502946, compoundYield 19%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 8.58 g (34.5 mmol) of 3,3-bismethylthio-2-propionylacrylic acid ethyl ester, 8.67 g (34.5 mmol) of 4-bromo-2,6-dimethylphenylhydrazine hydrochloride and 7.31 g (69.0 mmol) of sodium carbonate in 150 mL of ethanol in a 250 mL RBF under an atmosphere of dry N2 was refluxed over the weekend. The reaction mixture was cooled to room temperature and evaporated to a reddish solid. This material was partitioned between 150 mL of water and 200 mL of methylene chloride (CH2Cl2). The organic layer was separated, dried over sodium sulfate and evaporated to a gum which was chromatographed on a silica gel column eluting with CH2Cl2 to give 2.6 g of pure product as a yellow oil. 1H-NMR (CDCl3) δ 1.26 (3H, t, J=7), 1.40 (3H, t, J=7), 1.94 (6H, s), 2.33 (3H, s), 2.93 (2H, q, J=7), 4.36 (2H, q, J=7), 7.30 (2H, s).

Workup

  1. customevaporated to a reddish solid
  2. customThis material was partitioned between 150 mL of water and 200 mL of methylene chloride (CH2Cl2)
  3. customThe organic layer was separated
  4. dry with materialdried over sodium sulfate
  5. customevaporated to a gum which
  6. customwas chromatographed on a silica gel column
  7. washeluting with CH2Cl2

Sources & evidence

ORD record
ord-33533745ba2d47268a95baf2bbef720c
Source dataset
uspto-grants-1999_10
Patent number
US05968944

Reaction notes

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