4-(Methylthio)benzaldehyde → HCID 54530667, compound

HRID 442749Notes

Reaction equation

HRID 442749 reaction equation
C[O-].[Na+].[CH3:4][S:5][C:6]1[CH:13]=[CH:12][C:9]([CH:10]=O)=[CH:8][CH:7]=1.[N:14]([CH2:17][C:18]([O:20][CH3:21])=[O:19])=[N+:15]=[N-:16]>CO.O>[CH3:21][O:20][C:18](=[O:19])[C:17]([N:14]=[N+:15]=[N-:16])=[CH:10][C:9]1[CH:12]=[CH:13][C:6]([S:5][CH3:4])=[CH:7][CH:8]=1

Participants

6

Reactant 3

HCID 769854-(Methylthio)benzaldehydeHCID 4020482Methyl 2-azidoacetateHCID 10942334Sodium Methoxide

Product 1

HCID 54530667HCID 54530667, compoundYield 82.2%

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 962WaterSolvent

Procedure

To a solution of sodium methoxide prepared from Na metal (8.65 g, 0.38 m) in methanol(200 mL) at 0°-5° C., was added a solution of 4-(methylthio)benzaldehyde (12.6 ml, 94.7 mmol) and methyl azidoacetate (44 g, 0.382 mol) in methanol (30 mL). After stirring at the same temperature for 3 hours, the suspension was diluted with H2O (300 mL). The solids were filtered, washed with water and dried under vacuum to provide 19.4 g (82.0%) of methyl-2-azido-3-(4-methylthiophenyl)propenoate as a yellow solid.

Workup

  1. filtrationThe solids were filtered
  2. washwashed with water
  3. customdried under vacuum

Sources & evidence

ORD record
ord-23a0c40aaf55467fbbb06f76399b62a7
Source dataset
uspto-grants-1999_04
Patent number
US05891901

Reaction notes

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