Acetic Acid → Fluproquazone

HRID 1578507Notes

Reaction equation

HRID 1578507 reaction equation
[CH:1]([NH:4][C:5]1[CH:19]=[C:18]([CH3:20])[CH:17]=[CH:16][C:6]=1[C:7]([C:9]1[CH:14]=[CH:13][C:12]([F:15])=[CH:11][CH:10]=1)=O)([CH3:3])[CH3:2].[N-:21]=[C:22]=[O:23].[K+].C(O)(=O)C>O>[CH:1]([N:4]1[C:5]2[C:6](=[CH:16][CH:17]=[C:18]([CH3:20])[CH:19]=2)[C:7]([C:9]2[CH:14]=[CH:13][C:12]([F:15])=[CH:11][CH:10]=2)=[N:21][C:22]1=[O:23])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 11051572Potassio isocyanateHCID 13431737(4-Fluorophenyl){4-methyl-2-[(propan-2-yl)amino]phenyl}methanone

Product 1

HCID 38503Fluproquazone

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 8.5 g. of 2-isopropylamino-4-methyl-4'-fluoro-benzophenone and 4.2 g. of potassium isocyanate in 100 ml. of glacial acetic acid is stirred at 60°-70°C. for 20 hours. The resulting mixture is treated with a mixture of ice and water and extracted three times with methylene chloride. The organic phases are combined, washed twice with water, once with sodium bicarbonate solution and again with water followed by drying and evaporation in vacuo. The residue is dissolved in a small amount of methylene chloride and precipitated by adding pentane. The resulting solid is redissolved in methylene chloride, treated with charcoal and diethyl ether exchanged for the methylene chloride to obtain a solid which is dried in a high vacuum at 60°C. to yield 1-isopropyl-7-methyl-4-(p-fluorophenyl)-2(1H)-quinazolinone, m.p. 172°-174°C.

Workup

  1. extractionextracted three times with methylene chloride
  2. washwashed twice with water, once with sodium bicarbonate solution and again with water
  3. customby drying
  4. customevaporation in vacuo
  5. dissolutionThe residue is dissolved in a small amount of methylene chloride
  6. customprecipitated
  7. additionby adding pentane
  8. dissolutionThe resulting solid is redissolved in methylene chloride
  9. additiontreated with charcoal and diethyl ether
  10. customto obtain a solid which
  11. customis dried in a high vacuum at 60°C.

Sources & evidence

ORD record
ord-bf6a8ba6c375486bafac1f0d0d93b419
Source dataset
uspto-grants-1976_02
Patent number
US03937705

Reaction notes

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