Dimethylformamide → HCID 178519879, compound

HRID 526744Notes

Reaction equation

HRID 526744 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5](/[C:8](=[N:10]/[NH:11][C:12](N)=O)/[CH3:9])=[CH:4][CH:3]=1.P(Cl)(Cl)(Cl)=O.CN(C)[CH:22]=[O:23]>>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[C:9]([CH:22]=[O:23])=[CH:12][NH:11][N:10]=2)=[CH:6][CH:7]=1

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 24813Phosphorus oxychlorideHCID 9583323HCID 9583323, compound

Product 1

HCID 178519879HCID 178519879, compoundYield 62%

Conditions

Temperature
70 °C

Procedure

To a stirred solution of (E)-2-(1-(4-fluorophenyl)ethylidene)hydrazinecarboxamide (1 g, 5.12 mmol, 1.00 equiv) in N,N-dimethylformamide (5 mL) at 5° C. was added phosphorous oxychloride (5 mL) dropwise. The resulting solution was stirred at 70° C. for 2 h. The reaction mixture was cooled to 0° C. and quenched by the addition of 15 mL of ice/water mixture. The pH value of the solution was adjusted to 7 with 4N sodium hydroxide solution. The resulting mixture was stirred at 70° C. for an additional 1 h. The reaction mixture was cooled back to room temperature. The precipitate was collected by filtration and dried in a vacuum oven to give 600 mg (62%) of 3-(4-fluorophenyl)-1H-pyrazole-4-carbaldehyde as a gray solid. LCMS (method A, ESI): RT=1.23 min, m/z=191.0 [M+H]+.

Workup

  1. temperatureThe reaction mixture was cooled to 0° C.
  2. customquenched by the addition of 15 mL of ice/water mixture
  3. stirringThe resulting mixture was stirred at 70° C. for an additional 1 h
  4. temperatureThe reaction mixture was cooled back to room temperature
  5. filtrationThe precipitate was collected by filtration
  6. customdried in a vacuum oven

Sources & evidence

ORD record
ord-deca7a416e3e4f09bfe9c8fec88af65f
Source dataset
uspto-grants-2016_05
Patent number
US09346761B2

Reaction notes

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