Water → HCID 19387925, compound

HRID 1757402Notes

Reaction equation

HRID 1757402 reaction equation
O[N:2]1[C:6](=[O:7])[C:5]2=[CH:8][CH:9]=[CH:10][CH:11]=[C:4]2[C:3]1=[O:12].[C:13]([O:17][K])(C)(C)[CH3:14].C(CCl)#[N:20].O>CN(C=O)C>[C:14]([CH2:13][O:17][C:8]1[CH:9]=[CH:10][CH:11]=[C:4]2[C:3]([NH:2][C:6](=[O:7])[C:5]=12)=[O:12])#[N:20]

Participants

6

Reactant 4

HCID 962WaterHCID 7856ChloroacetonitrileHCID 10665N-HydroxyphthalimideHCID 178418922HCID 178418922, compound

Product 1

HCID 19387925HCID 19387925, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a mixture of 16.8 g (0.1 mol) N-hydroxyphthalimide and 12.7 g (0.11 mol)tert-BuOK in 150 mL DMF under stirring was added cyanomethyl chloride (7.8 g, 0.1 mol). Discoloration of the reaction mixture occurred in 10 min. After 24 h of stirring at room temperature the mixture was poured into 750mL of cold H2O. Precipitate was filtered off and dried under vacuum in the presence of anhydrous CaSO4 to yield about 10 g (50%) of cyanomethoxyphthalimide. To a solution of 10 g (0.05 mol) cyanomethoxyphthalimide in 50 mL THF was added dropwise at room temperature during 2 h a solution of 2.5 mL (0.05 mol) hydrazine-hydrate (100%) in 10 mL MeOH. After additional stirring for 2 h the mixture was acidified under ice-cooling with 25 mL of 2M solution (0.05 mol) HCl and the resulting mixture was stirred at this temperature for 30 min. The insoluble material was filtered off, filtrate adjusted to pH 7 with 2M NaOH. The product was then extracted 4 times with EtOAc, the combined organics were washed with brine, and dried over anhydrous Na2SO4. The solution was concentrated in vacuo, the residue was dissolved in ether and treated with an excess of dry hydrogen chloride. The title compound, a precipitate, was filtered off and dried under vacuumin the presence of anhydrous CaSO4.

Workup

  1. stirringAfter 24 h of stirring at room temperature the mixture
  2. filtrationPrecipitate was filtered off
  3. dry with materialdried under vacuum in the presence of anhydrous CaSO4

Sources & evidence

ORD record
ord-4f7c2015e0a449d89a927db8aa3b99aa
Source dataset
uspto-grants-1995_08
Patent number
US05446048

Reaction notes

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