4-Methoxybenzaldehyde → HCID 13537743, compound

HRID 1583970Notes

Reaction equation

HRID 1583970 reaction equation
Cl[C:2]1[C:6]([C:7]2[CH:12]=[CH:11][C:10]([O:13][CH3:14])=[CH:9][CH:8]=2)=[N:5][S:4][N:3]=1.C(=O)C1C=C[C:19]([O:22]C)=CC=1.C[O-].[Na+]>CN(C)C=O>[CH3:19][O:22][C:2]1[C:6]([C:7]2[CH:12]=[CH:11][C:10]([O:13][CH3:14])=[CH:9][CH:8]=2)=[N:5][S:4][N:3]=1

Participants

5

Reactant 3

HCID 312444-MethoxybenzaldehydeHCID 10942334Sodium Methoxide2×HCID 13537732HCID 13537732, compound

Product 1

HCID 13537743HCID 13537743, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Under a dry nitrogen atmosphere 3.0 g (0.0013 mole) of 3-chloro-4-(4-methoxyphenyl)-1,2,5-thiadiazole (prepared by the method of Example 2 from p-anisaldehyde) was added to a stirred suspension of 0.78 g (0.0015 mole) of anhydrous sodium methoxide in 30 ml of N,N-dimethylformamide. The reaction mixture became exothermic. The mixture was allowed to cool slowly to room temperature and stir for approximately 18 hours. Approximately 0.1 g of anhydrous sodium methoxide was added and the mixture stirred an additional three hours. The reaction mixture was poured into 250 ml of ice water and the total extracted with diethyl ether. The ether extract was washed with water, dried over anhydrous magnesium sulfate and filtered. The solvent was evaporated from the filtrate under reduced pressure to leave a beige solid. The solid was chromatographed on silica gel, eluted with methylene chloride to give a yellow solid. The yellow solid was purified by column chromatography on silica gel, eluted with n-hexane:ethyl acetate (7:1) to yield 0.7 g of 3-methoxy-4-(4-methoxyphenyl)-1,2,5 -thiadiazole, Compound 32 of Table I.

Workup

  1. stirringthe mixture stirred an additional three hours
  2. extractionthe total extracted with diethyl ether
  3. extractionThe ether extract
  4. washwas washed with water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. customThe solvent was evaporated from the filtrate under reduced pressure
  8. customto leave a beige solid
  9. customThe solid was chromatographed on silica gel
  10. washeluted with methylene chloride
  11. customto give a yellow solid
  12. customThe yellow solid was purified by column chromatography on silica gel
  13. washeluted with n-hexane:ethyl acetate (7:1)

Sources & evidence

ORD record
ord-d8fd7159f50a406ca5a4e28cc183a0cb
Source dataset
uspto-grants-1985_11
Patent number
US04555521

Reaction notes

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