2-Methylbenzoic acid → Mepronil

HRID 1578625Notes

Reaction equation

HRID 1578625 reaction equation
[CH3:1][C:2]1[CH:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=O.[CH:11]([O:14][C:15]1[CH:16]=[C:17]([CH:19]=[CH:20][CH:21]=1)[NH2:18])([CH3:13])[CH3:12].C(N(CC)CC)C.P(Cl)(Cl)(Cl)=O>C1(C)C(C)=CC=CC=1>[CH:11]([O:14][C:15]1[CH:16]=[C:17]([CH:19]=[CH:20][CH:21]=1)[NH:18][C:4](=[O:6])[C:3]1[CH:7]=[CH:8][CH:9]=[CH:10][C:2]=1[CH3:1])([CH3:13])[CH3:12]

Participants

6

Reactant 4

HCID 83732-Methylbenzoic acidHCID 8471TriethylamineHCID 24813Phosphorus oxychlorideHCID 5732203-(Propan-2-yloxy)aniline

Product 1

HCID 41632MepronilYield 77.9%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

A 13.6 g (0.1 mol) portion of o-methylbenzoic acid, 15.1 g (0.1 mol) of m-isopropoxyaniline and 10.1 g (0.1 mol) of triethylamine were dissolved in 100 ml of xylene. A 5.1 g (0.033 mol) amount of phosphorus oxychloride was added dropwise to the prepared solution with stirring at 90°-100°C. Stirring of the resulting solution was continued at 90°-100°C for 3 hours. The reaction mixture was cooled and washed with water, and the product was dried over anhydrous sodium sulfate. The xylene was removed to obtain 20.9 g (77.9%) of white prismatic crystals having a melting point of 92°-94°C.

Workup

  1. stirringStirring of the resulting solution
  2. temperatureThe reaction mixture was cooled
  3. washwashed with water
  4. dry with materialthe product was dried over anhydrous sodium sulfate
  5. customThe xylene was removed

Sources & evidence

ORD record
ord-564dd7a8a29b4e318a4e490e61366029
Source dataset
uspto-grants-1976_02
Patent number
US03937840

Reaction notes

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