Acetonitrile → HCID 20064747, compound

HRID 359286Notes

Reaction equation

HRID 359286 reaction equation
C(#N)C.[CH:4]([NH2:7])([CH3:6])[CH3:5].Cl[C:9]1[S:10][C:11]([C:18]([O:20][CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[O:19])=[C:12]([C:14]([F:17])([F:16])[F:15])[N:13]=1>C(OCC)C>[CH3:5][CH:4]([NH:7][C:9]1[S:10][C:11]([C:18]([O:20][CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[O:19])=[C:12]([C:14]([F:16])([F:15])[F:17])[N:13]=1)[CH3:6]

Participants

5

Reactant 3

HCID 6342AcetonitrileHCID 6363IsopropylamineHCID 91715Flurazole

Product 1

HCID 20064747HCID 20064747, compoundYield 62%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A reaction vessel was charged with 25 ml of acetonitrile, 2.94 g (49.8 mmol) of iso-propylamine, and 8 g (24.9 mmol) of benzyl 2-chloro-4-trifluoromethyl-5-thiazolecarboxylate (prepared as described in U.S. Pat. No. 4,199,506). The reaction mixture was heated at reflux for 16 hours. The mixture was then cooled to ambient temperature, diluted with ethyl ether, washed with large amounts of water, dried over magnesium sulfate, and concentrated under reduced pressure to yield 5.32 g of a gold oil. This oil was subjected - to Kugelrohr distillation (145°-155° C. @ 0.5 mm Hg) to yield 4.97 of a gold oil which was then triturated in hexane to yield 3.99 g of a yellow solid product (m.p.=49°-53° C.) identified in Table I.

Workup

  1. customprepared
  2. temperatureThe reaction mixture was heated
  3. temperatureat reflux for 16 hours
  4. washwashed with large amounts of water
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-11fb6164c4c545a89af5d250b561c05d
Source dataset
uspto-grants-1991_03
Patent number
US05000775

Reaction notes

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