Phosgene → 6-Fluoroisatoic anhydride

HRID 67450Notes

Reaction equation

HRID 67450 reaction equation
[C:1](Cl)(Cl)=[O:2].Cl.[F:6][C:7]1[CH:8]=[CH:9][CH:10]=[C:11]([NH2:16])[C:12]=1[C:13]([OH:15])=[O:14]>O1CCCC1.Cl>[F:6][C:7]1[CH:8]=[CH:9][CH:10]=[C:11]2[NH:16][C:1](=[O:2])[O:15][C:13](=[O:14])[C:12]=12

Participants

5

Reactant 2

HCID 6371PhosgeneHCID 250673672-Amino-6-fluorobenzoic acid hydrochloride

Product 1

HCID 27830576-Fluoroisatoic anhydride

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 8028TetrahydrofuranSolvent

Procedure

Phosgene is conducted at 35°-40° C. for 3 hours into a solution of 23 g (0.148 mol) of 6-fluoroanthranilic acid hydrochloride in a mixture of 300 ml of tetrahydrofuran and 150 ml of 4 N hydrochloric acid. After removal of the phosgene, the mixture is diluted with 500 ml of water and the precipitate is filtered off. There is obtained crude 6-fluoroisatoic acid anhydride of melting point 265°-267° C. (decomposition).

Workup

  1. customAfter removal of the phosgene
  2. additionthe mixture is diluted with 500 ml of water
  3. filtrationthe precipitate is filtered off

Sources & evidence

ORD record
ord-19986f6e072e4569bd56f5853551d4c6
Source dataset
uspto-grants-1982_08
Patent number
US04346034

Reaction notes

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