Phosgene → HCID 13424424, compound

HRID 1980489Notes

Reaction equation

HRID 1980489 reaction equation
[C:1](=O)([O-])[O-:2].[K+].[K+].[CH3:7][O:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[NH:15][C:16]1[CH:24]=[CH:23][CH:22]=[CH:21][C:17]=1[C:18]([OH:20])=[O:19].C(Cl)(Cl)=O>C1(C)C=CC=CC=1.O>[CH3:7][O:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[N:15]1[C:1](=[O:2])[O:20][C:18](=[O:19])[C:17]2=[CH:21][CH:22]=[CH:23][CH:24]=[C:16]12

Participants

6

Reactant 3

HCID 6371PhosgeneHCID 11430Potassium CarbonateHCID 202774Anthranilic acid, N-(2-methoxyphenyl)-

Product 1

HCID 13424424HCID 13424424, compoundYield 22.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

To a suspension of 24.44 g (0.177 mole) of potassium carbonate in 119 ml of toluene and 238 ml of water, stirred at 20°-40° C., was added 28.61 g (0.1176 mole) of 2-(2-methoxyphenylamino)benzoic acid, and phosgene was bubbled through the mixture for a period of 3.5 hours. The reaction was allowed to stand overnight with stirring, and the solid material was collected by filtration. The latter was dissolved in ethyl acetate and added to the toluene layer separated from the filtrate. The solution was washed twice with 200 ml 1N potassium hydroxide and dried over anhydrous magnesium sulfate. The solvent was removed in vacuo to yield 7 g of N-(2-methoxyphenyl)isatoic anhydride.

Workup

  1. customwas bubbled through the mixture for a period of 3.5 hours
  2. stirringwith stirring
  3. filtrationthe solid material was collected by filtration
  4. dissolutionThe latter was dissolved in ethyl acetate
  5. additionadded to the toluene layer
  6. customseparated from the filtrate
  7. washThe solution was washed twice with 200 ml 1N potassium hydroxide
  8. dry with materialdried over anhydrous magnesium sulfate
  9. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-51ed0e3dc4dd40a9bcc9792b6e5ab8d7
Source dataset
uspto-grants-1985_04
Patent number
US04510139

Reaction notes

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