Acetic Acid → Flumiclorac-pentyl

HRID 704473Notes

Reaction equation

HRID 704473 reaction equation
[Cl:1][C:2]1[C:8]([O:9][CH2:10][C:11]([O:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])=[O:12])=[CH:7][C:5]([NH2:6])=[C:4]([F:19])[CH:3]=1.[C:20]1(=O)[O:25][C:23](=[O:24])[C:22]2[CH2:26][CH2:27][CH2:28][CH2:29][C:21]1=2.N1CCCCC1.C(O)(=O)C>O.C1(C)C=CC=CC=1>[Cl:1][C:2]1[C:8]([O:9][CH2:10][C:11]([O:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])=[O:12])=[CH:7][C:5]([N:6]2[C:23](=[O:24])[C:22]3[CH2:26][CH2:27][CH2:28][CH2:29][C:21]=3[C:20]2=[O:25])=[C:4]([F:19])[CH:3]=1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 8082PiperidineHCID 124753,4,5,6-Tetrahydrophthalic anhydrideHCID 146178504-Chloro-2-fluoro-5-(pentyloxycarbonylmethyloxy)aniline

Product 1

HCID 443048Flumiclorac-pentylYield 95.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

A mixture of the compound (II) (12.0 g), 3,4,5,6-tetrahydrophthalic anhydride (7.56 g), piperidine (0.36 g), acetic acid (0.5 g) and toluene (24 g) was refluxed at 88° to 92° C. under a pressure of about 300 mmHg for 4 hours, during which water was azeotropically removed. The reaction mixture was then treated as in Example 4 to give the compound (I) (16.7 g).

Workup

  1. customwas azeotropically removed
  2. additionThe reaction mixture was then treated as in Example 4

Sources & evidence

ORD record
ord-956d1aa9e0b14fc297b7a1a378834c15
Source dataset
uspto-grants-1991_01
Patent number
US04987247

Reaction notes

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