Dimethylformamide → SBB016247

HRID 615026Notes

Reaction equation

P(Cl)(Cl)(Cl)=O.[C:6]1([N:12]2[C:16]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)=[CH:15][C:14]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)=[N:13]2)[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.CN(C)[CH:31]=[O:32]>>[C:6]1([N:12]2[C:16]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)=[C:15]([CH:31]=[O:32])[C:14]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)=[N:13]2)[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

Reactant 3

HCID 6228Dimethylformamide

HCID 24813Phosphorus oxychloride

HCID 6266141,3,5-Triphenylpyrazole

Product 1

HCID 693320SBB016247Yield 80.4%

Procedure

32 grams phosphorus oxychloride were added dropwise at 0°-5° C. to 75 grams dimethylformamide. The mixture was thereafter stirred for 1 hours at room temperature. Thereafter, 25 grams 1,3,5-triphenyl-pyrazol were added to the mixture, which was then stirred for 8 hours at 80° C. The reaction mixture, which was evaporated and water added to the residue. The pH of the aqueous mixture was adjusted to 8-10. The precipitate was separated and crystallized from ethanol. 22 grams 1,3,5-triphenyl-pyrazol-4-aldehyde, melting at 159°-160° C., were obtained, representing a yield of 80%.

Workup

stirringwas then stirred for 8 hours at 80° C
customThe reaction mixture, which was evaporated
additionwater added to the residue
customThe precipitate was separated
customcrystallized from ethanol

Sources & evidence

ORD record: ord-a5db03f3199447e49436cb037f94eedb
Source dataset: uspto-grants-1979_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04146721

Reaction notes

Loading…