Sodium Chloride → HCID 19876601, compound

HRID 1885973Notes

Reaction equation

HRID 1885973 reaction equation
Cl.[Cl:2][C:3]1[CH:4]=[CH:5][CH:6]=[C:7]([NH2:12])[C:8]=1[C:9]([OH:11])=[O:10].[CH2:13](Cl)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.C(=O)(O)[O-].[K+].[Cl-].[Na+]>CN(C)C=O>[Cl:2][C:3]1[CH:4]=[CH:5][CH:6]=[C:7]([NH2:12])[C:8]=1[C:9]([O:11][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[O:10]

Participants

6

Reactant 4

HCID 5234Sodium ChlorideHCID 7503Benzyl ChlorideHCID 516893Potassium BicarbonateHCID 53444447HCID 53444447, compound

Product 1

HCID 19876601HCID 19876601, compoundYield 78.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Under a nitrogen atmosphere a solution of 6.4 grams (0.031 mole) of 6-chloroanthranilic acid hydrochloride (prepared as in Example 3, Step B), 3.9 grams (0.031 mole) of benzyl chloride, and 6.2 grams (0.062 mole) of potassium bicarbonate in 100 mL of dimethylformamide was stirred at ambient temperature for about 48 hours. After this time the reaction mixture was poured into 250 mL of an aqueous solution saturated with sodium chloride. The mixture was extracted with three 250 mL portions of diethyl ether. The combined extracts were washed with one 250 mL portion of an aqueous solution saturated with sodium chloride. The organic layer was dried with magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure to a residue. The residue was subjected to column chromatography on silica gel. Elution was accomplished using 20% ethyl acetate in heptane. The appropriate fractions were combined and concentrated under reduced pressure to yield 6.4 grams of phenylmethyl 6-chloroanthranilate. The nmr spectrum was consistent with the proposed structure.

Workup

  1. extractionThe mixture was extracted with three 250 mL portions of diethyl ether
  2. washThe combined extracts were washed with one 250 mL portion of an aqueous solution saturated with sodium chloride
  3. dry with materialThe organic layer was dried with magnesium sulfate
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated under reduced pressure to a residue
  6. washElution
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-5acd98bb97884619875739dceb6fc9c6
Source dataset
uspto-grants-1992_09
Patent number
US05149357

Reaction notes

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