Potassium Hydroxide → HCID 178516141, compound

HRID 1765223Notes

Reaction equation

HRID 1765223 reaction equation
[F:1][C:2]([F:13])([F:12])[C:3]1[N:8]=[CH:7][C:6]([C:9]([NH2:11])=[NH:10])=[CH:5][CH:4]=1.[F:14][C:15]([F:24])([F:23])[C:16]#[C:17][C:18](OCC)=[O:19].[OH-].[K+]>C(O)C>[OH:19][C:18]1[CH:17]=[C:16]([C:15]([F:24])([F:23])[F:14])[N:11]=[C:9]([C:6]2[CH:7]=[N:8][C:3]([C:2]([F:12])([F:1])[F:13])=[CH:4][CH:5]=2)[N:10]=1

Participants

5

Reactant 3

HCID 14797Potassium HydroxideHCID 27607786-(Trifluoromethyl)pyridine-3-carboximidamideHCID 3597254Ethyl 4,4,4-trifluoro-2-butynoate

Product 1

HCID 178516141HCID 178516141, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
0 °C

Procedure

A mixture of 6-(trifluoromethyl)pyridine-3-amidine (1 g, 5.26 mmol) and ethyl 4,4,4-trifluoro-2-butynoate (1.1 ml, 7.89 mmol) in ethanol (100 ml) was stirred at 0° C. for 20 min. The temperature of the mixture was raised to 60° C. and was let to stir at this temperature for 30 min. Then aqueous KOH (0.86 g in 20 ml water) was added dropwise. The mixture was refluxed for 4 h. The mixture was cooled to room temperature, rotary evaporated and isolated as a white solid (1.5 g, 94%). 1H NMR (CDCl3): 9.72 (d, J=2.4 Hz, 1H), 8.87 (dd, J=2.1, 8.7 Hz, 1H), 7.93 (d, J=8.1 Hz, 1H), 7.00 (s, 1H).

Workup

  1. temperatureThe temperature of the mixture was raised to 60° C.
  2. stirringto stir at this temperature for 30 min
  3. temperatureThe mixture was refluxed for 4 h
  4. temperatureThe mixture was cooled to room temperature
  5. customrotary evaporated

Sources & evidence

ORD record
ord-a8e2c6b91d824227bc2e083c0fb3c29f
Source dataset
uspto-grants-2007_06
Patent number
US07226927B2

Reaction notes

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