Potassium Hydroxide → HCID 15036429, compound

HRID 1534109Notes

Reaction equation

HRID 1534109 reaction equation
F[C:2]1[CH:7]=[CH:6][C:5]([C:8]([CH2:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)([CH2:11][N:12]2[CH:16]=[N:15][CH:14]=[N:13]2)[C:9]#[N:10])=[CH:4][CH:3]=1.[OH-].[K+].N1C=CN=N1.BrCC(C#N)(C1C=CC=CC=1)CCC1C=CC=C([C:43]([F:46])([F:45])[F:44])C=1>CS(C)=O.C(OCC)(=O)C.O.C1(C)C=CC=CC=1>[C:5]1([C:8]([CH2:17][CH2:18][C:19]2[CH:20]=[CH:21][CH:22]=[C:23]([C:43]([F:46])([F:45])[F:44])[CH:24]=2)([CH2:11][N:12]2[CH:16]=[N:15][CH:14]=[N:13]2)[C:9]#[N:10])[CH:4]=[CH:3][CH:2]=[CH:7][CH:6]=1

Participants

9

Reactant 4

HCID 14797Potassium HydroxideHCID 15036428HCID 15036428, compoundHCID 15036451HCID 15036451, compoundHCID 178418936HCID 178418936, compound

Product 1

HCID 15036429HCID 15036429, compoundYield 76.7%

Reagents, catalysts & solvents 4

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolventHCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
100 °C

Procedure

A 250 ml 4 neck round bottom flask was charged with 4.05 gms of 87% KOH (0.062 mole, 1.25 eq.) and 4.8 gms (0.068 mole, 2.2 eq.) of triazole in 25 ml DMSO. The reaction was warmed to 90° C. until homogeneous and 25 ml of toluene was added and azeotroped for 4 hours. The toluene was distilled off at 165° C. and the reaction was cooled to 100° C. and 12.5 g of 1-bromo-2-cyano-2-phenyl-4-(3-trifluoromethylphenyl)butane (0.031 mole, 1.0 eq.) was added. The reaction was heated at 125° C. for 1 hour and then worked up with water and ethyl acetate, dried and concentrated. Purification by high pressure liquid chromatography (1:1) hexane:ethyl acetate gave 8.8 gms of a white solid having a melting point of 127°-128° C. (76.7% yield).

Workup

  1. additionwas added
  2. customazeotroped for 4 hours
  3. distillationThe toluene was distilled off at 165° C.
  4. temperatureThe reaction was heated at 125° C. for 1 hour
  5. customdried
  6. concentrationconcentrated
  7. customPurification by high pressure liquid chromatography (1:1) hexane

Sources & evidence

ORD record
ord-787704794f00434fa101c83182d99c21
Source dataset
uspto-grants-1992_02
Patent number
US05087635

Reaction notes

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