Sodium Hydroxide → Fenoxanil

HRID 1586277Notes

Reaction equation

C(=O)(O)[O-].[Na+].[NH2:6][C:7]([CH3:13])([CH:10]([CH3:12])[CH3:11])[C:8]#[N:9].[Cl:14][C:15]1[CH:26]=[C:25]([Cl:27])[CH:24]=[CH:23][C:16]=1[O:17][C@H:18]([CH3:22])[C:19](Cl)=[O:20].[OH-].[Na+]>O.C1(C)C=CC=CC=1>[C:8]([C:7]([NH:6][C:19](=[O:20])[CH:18]([O:17][C:16]1[CH:23]=[CH:24][C:25]([Cl:27])=[CH:26][C:15]=1[Cl:14])[CH3:22])([CH3:13])[CH:10]([CH3:12])[CH3:11])#[N:9]

Participants

Conditions

Temperature: 55 °C

Procedure

A stirred mixture of sodium bicarbonate (1.446 kg; 17.2 mol) in water at -3° to 3° C. is treated with a toluene solution of 2-amino-2,3-dimethylbutyronitrile (1.51 kg, 13.46 mol) over a 15 minute period, then treated sequentially with a toluene solution of (R)-2-(2,4-dichlorophenoxy)propionyl chloride (3.346 kg, 13.2 mol) over a 1.5 hour period at ice bath temperatures, stirred for 0.5 hours, treated with 50% NaOH (0.396 kg), heated to 55° C. and stirred for 0.5 hours. The resultant mixture is separated. The organic phase is washed with 5% NaOH and distilled at temperatures up to 80° C. at 10 mm Hg to remove the toluene. The pot residue is crystallized in isopropanol/water to afford the title product as a white solid, 4.131 kg (94.8% yield), characterized by HPLC analysis. The product is 99.7% pure. The isomer ratio is: 94.8% RR, RS and 5.2% SS, SR.

Workup

stirringstirred for 0.5 hours
customThe resultant mixture is separated
washThe organic phase is washed with 5% NaOH
distillationdistilled at temperatures up to 80° C. at 10 mm Hg
customto remove the toluene
customThe pot residue is crystallized in isopropanol/water

Sources & evidence

ORD record: ord-0602422394ff4cdc8845654e77c9aae5
Source dataset: uspto-grants-1999_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05942640

Reaction notes

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