Dimethylformamide → Chloro-N,N-dimethylformiminium chloride

HRID 429660Notes

Reaction equation

HRID 429660 reaction equation
P(Cl)(Cl)(O[Cl:4])=O.[NH:7]1[C:15]2[CH:14]=[CH:13][CH:12]=[C:11]([C:16]([O:18][CH3:19])=[O:17])[C:10]=2[CH:9]=[CH:8]1.[C:20](=O)(O)[O-:21].[Na+].[CH3:25][N:26]([CH3:29])[CH:27]=O>O>[CH3:25][N+:26]([CH3:29])=[CH:27][Cl:4].[Cl-:4].[CH:20]([C:9]1[C:10]2[C:11]([C:16]([O:18][CH3:19])=[O:17])=[CH:12][CH:13]=[CH:14][C:15]=2[NH:7][CH:8]=1)=[O:21]

Participants

7

Reactant 4

HCID 6228Dimethylformamide2×HCID 516892Sodium BicarbonateHCID 2733668methyl 1H-indole-4-carboxylateHCID 86587839Phosphoryloxychloride

Product 2

HCID 77311Chloro-N,N-dimethylformiminium chlorideHCID 12396096methyl 3-formyl-1H-indole-4-carboxylate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

The Vilsmeier reagent was prepared by the dropwise addition of phosphoryl oxychloride (0.75 mg) to cooled N,N-dimethylformamide (20.0 ml) under constant stirring. A solution of methyl indole-4-carboxylate in N,N-dimethylformamide (12.0 ml) was added to the above solution at 0° C. and the solution was stirred for 30 minutes. The mixture was diluted with water (40 ml) and the solution was neutralized with saturated sodium bicarbonate aqueous solution and extracted with ethyl acetate (60 ml). The organic layer was washed successively with water and brine, dried over magnesium sulfate and concentrated invacuo. The solid was triturated with diethyl ether (7 ml) to give methyl 3-formylindole-4-carboxylate (792 mg).

Workup

  1. extractionextracted with ethyl acetate (60 ml)
  2. washThe organic layer was washed successively with water and brine
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated invacuo
  5. customThe solid was triturated with diethyl ether (7 ml)

Sources & evidence

ORD record
ord-1203d161aa3244788af5628542c77dca
Source dataset
uspto-grants-2001_11
Patent number
US06316482B1

Reaction notes

Loading…