Dimethylformamide → HCID 20064730, compound

HRID 359297Notes

Reaction equation

HRID 359297 reaction equation
CN(C)C=O.C(=O)([O-])[O-].[K+].[K+].[F:12][C:13]([F:23])([F:22])[C:14]1[CH:15]=[C:16]([CH:19]=[CH:20][CH:21]=1)[CH2:17]Cl.[CH3:24][C:25]([NH:28][C:29]1[O:30][C:31]([C:38]([OH:40])=[O:39])=[C:32]([C:34]([F:37])([F:36])[F:35])[N:33]=1)([CH3:27])[CH3:26]>O>[CH3:27][C:25]([NH:28][C:29]1[O:30][C:31]([C:38]([O:40][CH2:17][C:16]2[CH:19]=[CH:20][CH:21]=[C:14]([C:13]([F:23])([F:22])[F:12])[CH:15]=2)=[O:39])=[C:32]([C:34]([F:35])([F:37])[F:36])[N:33]=1)([CH3:24])[CH3:26]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 697163-(Trifluoromethyl)benzyl chlorideHCID 15812073HCID 15812073, compound

Product 1

HCID 20064730HCID 20064730, compoundYield 161.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A reaction vessel was charged with 50 ml of dimethylformamide, 2.6 g (18.8 mmol) of potassium carbonate, and 5.36 g (28 mmol) of m-trifluoromethyl benzyl chloride. With this mixture stirred at ambient temperature under a nitrogen atmosphere, there was added 4.03 g (17 mmol) of 2-[(1,1-dimethylethyl)amino]-4-trifluoromethyl-5-oxazolecarboxylic acid (prepared by Example 26). The reaction mixture was stirred at ambient temperature for 36 hours. Then, the mixture was added to water and extracted four times with ethyl ether. The ether extracts were washed with large amounts of water, then dried over magnesium sulfate, and concentrated under reduced pressure to yield 11.25 g of a yellow oily solid material. This solid material was dissolved in ethyl ether, washed with large amounts of water, dried over magnesium sulfate, and concentrated under reduced pressure to yield 10.8 g of a gold viscous oil. Then, 5.0 g of this oil was subjected to Kugelrohr distillation (83°-85° C. @ 0.5 mm Hg) to yield 1.38 g of a gold viscous oil which upon standing overnight formed an oily solid product identified in Table I.

Workup

  1. stirringThe reaction mixture was stirred at ambient temperature for 36 hours
  2. extractionextracted four times with ethyl ether
  3. washThe ether extracts were washed with large amounts of water
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-f41480956bf54120be82fca5e5f77391
Source dataset
uspto-grants-1991_03
Patent number
US05000775

Reaction notes

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