Acetic Acid → Flumiclorac-pentyl

HRID 704472Notes

Reaction equation

HRID 704472 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.C(N(CC)CC)C.C(O)(=O)C>ClCCCl>[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

6

Reactant 4

HCID 176Acetic AcidHCID 8471TriethylamineHCID 124753,4,5,6-Tetrahydrophthalic anhydrideHCID 146178504-Chloro-2-fluoro-5-(pentyloxycarbonylmethyloxy)aniline

Product 1

HCID 443048Flumiclorac-pentylYield 92.3%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

A mixture of the compound (II) (12.0 g), 3,4,5,6-tetrahydrophthalic anhydride (7.56 g), triethylamine (9.42 g), acetic acid (0.75 g) and 1,2-dichloroethane (24 g) was heated under reflux for 8 hours. The reaction mixture was washed with water (24 g). The organic layer was separated and treated as in Example 4 to give the compound (I) (16.2 g).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 8 hours
  3. washThe reaction mixture was washed with water (24 g)
  4. customThe organic layer was separated
  5. additiontreated as in Example 4

Sources & evidence

ORD record
ord-9bbaa1f07f2944a6a9bdb8297bcaf8c3
Source dataset
uspto-grants-1991_01
Patent number
US04987247

Reaction notes

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