Acifluorfen → HCID 13334851, compound

HRID 543908Notes

Reaction equation

HRID 543908 reaction equation
[Cl:1][C:2]1[CH:20]=[C:19]([C:21]([F:24])([F:23])[F:22])[CH:18]=[CH:17][C:3]=1[O:4][C:5]1[CH:6]=[CH:7][C:8]([N+:14]([O-:16])=[O:15])=[C:9]([CH:13]=1)[C:10]([OH:12])=O.[C:25]1([CH3:37])[CH:30]=[CH:29][C:28]([S:31]([N:34]=C=O)(=[O:33])=[O:32])=[CH:27][CH:26]=1>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:20]=[C:19]([C:21]([F:23])([F:22])[F:24])[CH:18]=[CH:17][C:3]=1[O:4][C:5]1[CH:6]=[CH:7][C:8]([N+:14]([O-:16])=[O:15])=[C:9]([CH:13]=1)[C:10]([NH:34][S:31]([C:28]1[CH:29]=[CH:30][C:25]([CH3:37])=[CH:26][CH:27]=1)(=[O:32])=[O:33])=[O:12]

Participants

4

Reactant 2

HCID 44073AcifluorfenHCID 77703p-Toluenesulfonyl isocyanate

Product 1

HCID 13334851HCID 13334851, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

A catalyst amount (ca. 10 gm) of N,N-dimethylaminopyridine (available from the Aldrich Chemical Co. Ltd.) was added to a stirred mixture of 5-(2-chloro-4-trifluoromethylphenoxy)-2-nitrobenzoic acid (260 gm, 0.72 moles) in 350 ml toluene under nitrogen. A solution of para-toluenesulfonylisocyanate (available from the Aldrich Chemical Co., Ltd., 180 gm, 0.94 moles) in toluene (150 ml) was then added dropwise to the above solution with stirring. After the addition was complete the mixture was brought to reflux for six hours. Toluene in the cooled solution was then removed in vacuo. The resulting waxy solid was further recrystalized from toluene to yield 170 gm (0.33 moles, 46%,) of the desired product.

Workup

  1. additionAfter the addition
  2. temperatureto reflux for six hours
  3. customToluene in the cooled solution was then removed in vacuo
  4. customThe resulting waxy solid was further recrystalized from toluene

Sources & evidence

ORD record
ord-2b04be1f6bdd471986bffb4409e416a9
Source dataset
uspto-grants-1984_05
Patent number
US04447634

Reaction notes

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