Toluene → HCID 53766389, compound

HRID 359269Notes

Reaction equation

HRID 359269 reaction equation
[CH3:1][NH:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[C:9]1(C)C=CC=C[CH:10]=1.Cl[C:17]1[O:18][C:19]([C:26]([O-:28])=[O:27])=[C:20]([C:22]([F:25])([F:24])[F:23])[N:21]=1>C(OCC)C>[CH3:1][N:2]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1)[C:17]1[O:18][C:19]([C:26]([O:28][CH2:9][CH3:10])=[O:27])=[C:20]([C:22]([F:25])([F:24])[F:23])[N:21]=1

Participants

5

Reactant 3

HCID 1140TolueneHCID 7515N-MethylanilineHCID 20064765HCID 20064765, compound

Product 1

HCID 53766389HCID 53766389, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

By the procedure of Example 15, 4.29 g (0.04 mol) of N-methyl aniline was added to 75 ml of toluene containing 4.87 g (0.02 mol) of 2-chloro-4-trifluoromethyl-5-oxazolecarboxylate. The reaction mixture was stirred at reflux for 72 hours. The product mixture was slurried in ethyl ether, washed with water and 25% sulfuric acid, dried and concentrated. The residue was distilled and the distillate recrystallized from a chloroformmethylcyclohexane solution to yield 3.5 g of a white-powder product (m.p.=78°-81° C.) identified in Table I.

Workup

  1. temperatureat reflux for 72 hours
  2. washwashed with water and 25% sulfuric acid
  3. customdried
  4. concentrationconcentrated
  5. distillationThe residue was distilled
  6. customthe distillate recrystallized from a chloroformmethylcyclohexane solution

Sources & evidence

ORD record
ord-b0d009b983b24be5ab7ba489a59dcc3b
Source dataset
uspto-grants-1991_03
Patent number
US05000775

Reaction notes

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