Dimethylformamide → HCID 15100874, compound

HRID 1090173Notes

Reaction equation

HRID 1090173 reaction equation
[K].[OH:2][N:3]1[CH:7]=CN=[N:4]1.Cl[C:9]([C:19]1[CH:24]=[CH:23][C:22]([F:25])=[CH:21][CH:20]=1)([C:12]1[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=1)[C:10]#[N:11].[CH3:26][N:27](C)C=O>>[C:10]([C:9]([C:19]1[CH:24]=[CH:23][C:22]([F:25])=[CH:21][CH:20]=1)([C:12]1[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=1)[O:2][N:3]1[CH:7]=[N:27][CH:26]=[N:4]1)#[N:11]

Participants

5

Reactant 4

HCID 6228Dimethylformamide2×HCID 5462222PotassiumHCID 10877052HCID 10877052, compoundHCID 15100873HCID 15100873, compound

Product 1

HCID 15100874HCID 15100874, compound

Procedure

1.5 g (12 mmol) of the potassium salt of N-hydroxytriazole in 20 ml of absolute dimethylformamide were initially taken under nitrogen. A solution of 3.16 g (12 mmol) of 2-chloro-2,2-di-(4-fluorophenyl)-acetonitrile in dimethylformamide was added dropwise to this solution, a slightly exothermic reaction taking place. The mixture was stirred for a further 3 hours at room temperature. The reaction solution was evaporated down, the residue was added to water and the mixture was extracted with ethyl acetate. The product was obtained from ethyl acetate in the form of a pale yellow oil, which crystallized out on stirring with diisopropyl ether.

Workup

  1. customa slightly exothermic reaction
  2. customThe reaction solution was evaporated down
  3. additionthe residue was added to water
  4. extractionthe mixture was extracted with ethyl acetate
  5. customThe product was obtained from ethyl acetate in the form of a pale yellow oil, which
  6. customcrystallized out
  7. stirringon stirring with diisopropyl ether

Sources & evidence

ORD record
ord-ef79c867c54c4a81a11801bf1bb7312d
Source dataset
uspto-grants-1992_01
Patent number
US05081142

Reaction notes

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