Potassium Hydroxide → HCID 57326486, compound

HRID 445254Notes

Reaction equation

HRID 445254 reaction equation
[CH2:1]([NH:9][C:10](=O)[C:11]1[CH:16]=[CH:15][C:14]([C:17]([F:20])([F:19])[F:18])=[CH:13][CH:12]=1)[CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.O=P12OP3(OP(OP(O3)(O1)=O)(=O)O2)=O.[OH-].[K+]>C(OCC)C>[F:18][C:17]([F:20])([F:19])[C:14]1[CH:15]=[CH:16][C:11]([C:10]2[C:8]3[C:3](=[CH:4][CH:5]=[CH:6][CH:7]=3)[CH2:2][CH2:1][N:9]=2)=[CH:12][CH:13]=1

Participants

5

Reactant 3

HCID 14797Potassium Hydroxide2×HCID 14812Phosphorus oxide (P4O10)HCID 706676HCID 706676, compound

Product 1

HCID 57326486HCID 57326486, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
165 °C

Procedure

To a 100-mL round-bottomed flask was added N-phenethyl-4-(trifluoromethyl)benzamide (5.0 g, 17 mmol), phosphoric pentoxide (0.526 mL, 8.52 mmol), and polyphosphoric acid (60.0 g). The reaction mixture was heated to 165° C. for 2 h. Then, the hot solution was carefully poured into ice/water and a solution of KOH (20%, 40 mL) was added to break up the oil. The mixture was stirred at RT for 5 min and an additional amount of KOH solution was added until pH 7. Ethyl ether (250 mL) was added and the mixture was stirred at RT for 15 min. The organic layer was collected and the aqueous layer was extracted with EtOAc (2×200 mL). The combined organic extracts were dried over MgSO4 and concentrated in vacuo to give the title compound as orange oil, which was used in the next step without further purification. MS (ESI, positive ion) m/z: 276 (M+H).

Workup

  1. stirringthe mixture was stirred at RT for 15 min
  2. customThe organic layer was collected
  3. extractionthe aqueous layer was extracted with EtOAc (2×200 mL)
  4. dry with materialThe combined organic extracts were dried over MgSO4
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-0ebd8bb6af99490686f9815d1b1e2900
Source dataset
uspto-grants-2013_07
Patent number
US08476297B2

Reaction notes

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