Water → HCID 19956225, compound

HRID 1779487Notes

Reaction equation

HRID 1779487 reaction equation
P(Cl)(Cl)(Cl)=O.[CH3:6][C:7]1[CH:8]=[CH:9][C:10]([N:16]2[CH:20]=[CH:19][CH:18]=[CH:17]2)=[C:11]([CH:15]=1)[C:12]([OH:14])=O.O>CN(C)C=O>[CH3:6][C:7]1[CH:8]=[CH:9][C:10]2[N:16]3[CH:20]=[CH:19][CH:18]=[C:17]3[C:12](=[O:14])[C:11]=2[CH:15]=1

Participants

5

Reactant 3

HCID 962WaterHCID 24813Phosphorus oxychlorideHCID 149135585-Methyl-2-(1H-pyrrol-1-yl)benzoic acid

Product 1

HCID 19956225HCID 19956225, compoundYield 35%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

At 0° C., add 1.36 ml (14.9 mmol) of phosphorus oxychloride to 1.14 ml (14.9 mmol) of dimethylformamide, then add a solution of 3 g (14.9 mmol) of 5-methyl-2-pyrrol-1-ylbenzoic acid (Preparation 25) in 30 ml of dimethylformamide. After one night's stirring at room temperature, hydrolyse the reaction mixture by pouring into 50 ml of water, extract with 200 ml of diethyl ether, and wash the ethereal phase in succession with water, a saturated aqueous hydrogen carbonate solution and then water. After drying over magnesium sulfate and rendering colourless with animal charcoal, the ethereal phase is concentrated to dryness to yield the title compound.

Workup

  1. extractionextract with 200 ml of diethyl ether
  2. washwash the ethereal phase in succession with water
  3. dry with materialAfter drying over magnesium sulfate and rendering colourless with animal charcoal
  4. concentrationthe ethereal phase is concentrated to dryness

Sources & evidence

ORD record
ord-386a5f86a788485f86c1969127f186a0
Source dataset
uspto-grants-1997_05
Patent number
US05627203

Reaction notes

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