Sodium Cyanide → Cyano(2,4-dioxo-1-propargyl-3-imidazolidinyl)methanol

HRID 2050346Notes

Reaction equation

HRID 2050346 reaction equation
[O:1]=[C:2]1[N:6]([CH:7]=[O:8])[C:5](=[O:9])[CH2:4][N:3]1[CH2:10][C:11]#[CH:12].[C-:13]#[N:14].[Na+].S(=O)(O)[O-].[Na+]>CCOCC.O>[C:13]([CH:7]([N:6]1[C:5](=[O:9])[CH2:4][N:3]([CH2:10][C:11]#[CH:12])[C:2]1=[O:1])[OH:8])#[N:14]

Participants

6

Reactant 3

HCID 8929Sodium CyanideHCID 203426582,4-Dioxo-1-propargyl-3-imidazolidine-carbaldehydeHCID 23665763Sodium Bisulfite

Product 1

HCID 20342650Cyano(2,4-dioxo-1-propargyl-3-imidazolidinyl)methanol

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 3283Diethyl EtherSolvent

Procedure

To a solution of 2,4-dioxo-1-propargyl-3-imidazolidine-carbaldehyde (1.8 mmol) in 25 ml of ether is added 25 ml of water followed by sodium cyanide (3.04 mmol). The mixture is stirred vigorously while a solution of sodium bisulfite (2.45 mmol) in 15 ml of water is added over about 5 minutes. The reaction mixture is stirred for two hours. The organic phase is separated, washed with water, dried over calcium sulfate and solvent evaporated to give cyano(2,4-dioxo-1-propargyl-3-imidazolidinyl)methanol.

Workup

  1. additionis added over about 5 minutes
  2. customThe organic phase is separated
  3. washwashed with water
  4. dry with materialdried over calcium sulfate and solvent
  5. customevaporated

Sources & evidence

ORD record
ord-bd696feb11a6475790143d41b9c225f4
Source dataset
uspto-grants-1980_04
Patent number
US04200758

Reaction notes

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