Ethanol → Mepronil

HRID 1287693

Reaction equation

HRID 1287693 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:15]=[CH:16][CH:17]=1)[NH:5][C:6](=[O:14])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[CH3:13].C(O)C.[CH:21](Br)([CH3:23])[CH3:22]>[OH-].[K+]>[CH:21]([O:1][C:2]1[CH:3]=[C:4]([CH:15]=[CH:16][CH:17]=1)[NH:5][C:6](=[O:14])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[CH3:13])([CH3:23])[CH3:22]

Participants

5

Reactant 3

HCID 702EthanolHCID 63582-Bromopropane2×HCID 11401898Benzamide, N-(3-hydroxyphenyl)-2-methyl-

Product 1

HCID 41632Mepronil

Reagents, catalysts & solvents 1

HCID 14797Potassium HydroxideSolvent

Procedure

A 22.7 g 0.1 mol) portion of 3'-hydroxy-2-methylbenzanilide was dissolved in 100 ml of 1N-potassium hydroxide solution. To this solution 150 ml of ethanol was added and the mixture was stirred for one hour, which was followed by the addition of 12.3 g (0.1 mol) of isopropylbromide. After the addition of the iso-propylbromide, the reaction mixture was warmed and stirred under reflux for 4 hours. After distillation of most of the ethanol, the oily material remaining was extracted with benzene and the residue was distilled to obtain 20.9 g (77.9%) of a red, viscous oil having a boiling point of 186° C/0.08 mm Hg. The product was recrystallized from a mixture of benzene and n-hexane (1 : 1) as white prismatic crystals having a melting point of 92° C. IR cm-1 (KBr-tablet) νNH 3250(S), νCH 2980(S), νCO 1660 (S), 1610(S).

Workup

  1. temperaturethe reaction mixture was warmed
  2. stirringstirred
  3. temperatureunder reflux for 4 hours
  4. distillationAfter distillation of most of the ethanol
  5. extractionthe oily material remaining was extracted with benzene
  6. distillationthe residue was distilled
  7. customto obtain 20.9 g (77.9%) of a red, viscous oil
  8. customThe product was recrystallized from a mixture of benzene and n-hexane (1 : 1) as white prismatic crystals

Sources & evidence

ORD record
ord-b579a333e5e24e3385d5fbb1ade06086
Source dataset
uspto-grants-1976_10
Patent number
US03985804

Linked notes

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