3,4,5,6-Tetrahydrophthalic anhydride → 1-[2-Chloro-4-fluoro-5-(1,2,3,4,5,6-hexahydro-1,3-dioxo-isoindolyl)-phenylthio]-cyclopropanecarboxylic acid

HRID 1646459Notes

Reaction equation

HRID 1646459 reaction equation
[NH2:1][C:2]1[C:3]([F:16])=[CH:4][C:5]([Cl:15])=[C:6]([S:8][C:9]2([C:12]([OH:14])=[O:13])[CH2:11][CH2:10]2)[CH:7]=1.[C:17]1(=O)[O:22][C:20](=[O:21])[C:19]2[CH2:23][CH2:24][CH2:25][CH2:26][C:18]1=2>C(O)(=O)C>[Cl:15][C:5]1[CH:4]=[C:3]([F:16])[C:2]([N:1]2[C:20](=[O:21])[CH:19]3[C:18](=[CH:26][CH2:25][CH2:24][CH2:23]3)[C:17]2=[O:22])=[CH:7][C:6]=1[S:8][C:9]1([C:12]([OH:14])=[O:13])[CH2:11][CH2:10]1

Participants

4

Reactant 2

HCID 124753,4,5,6-Tetrahydrophthalic anhydrideHCID 19800626HCID 19800626, compound

Product 1

HCID 678545381-[2-Chloro-4-fluoro-5-(1,2,3,4,5,6-hexahydro-1,3-dioxo-isoindolyl)-phenylthio]-cyclopropanecarboxylic acid

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of 2.4 g of 1-(5-amino-2-chloro-4-fluoro-phenylthio)-cyclopropanecarboxylic acid, 1.5 g of 3,4,5,6-tetrahydrophthalic anhydride and 100 ml of glacial acetic acid is heated under reflux for 18 hours while stirring. The reaction mixture is then introduced into ice-water and the resulting product is extracted with ethyl acetate. Drying over sodium sulfate and concentration of the solution by evaporation yield 1.7 g of 1-[2-chloro-4-fluoro-5-(1,2,3,4,5,6-hexahydro-1,3-dioxo-isoindolyl)-phenylthio]-cyclopropanecarboxylic acid having a melting point of from +186° to +188° C.

Workup

  1. temperatureis heated
  2. temperatureunder reflux for 18 hours
  3. extractionthe resulting product is extracted with ethyl acetate
  4. dry with materialDrying over sodium sulfate and concentration of the solution by evaporation yield 1.7 g of 1-[2-chloro-4-fluoro-5-(1,2,3,4,5,6-hexahydro-1,3-dioxo-isoindolyl)-phenylthio]-cyclopropanecarboxylic acid having a melting point of from +186° to +188° C.

Sources & evidence

ORD record
ord-946a8728182d4aaaa3ac4cf064e3b3c9
Source dataset
uspto-grants-1993_01
Patent number
US05180418

Reaction notes

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