Hydroquinone → N-Cyano-N'-propargyl-N"-(2-mercaptoethyl)guanidine

HRID 894133Notes

Reaction equation

HRID 894133 reaction equation
[C:1]([NH:3][C:4](=[N:7][CH2:8][C:9]#[CH:10])SC)#[N:2].Cl.[NH2:12][CH2:13][CH2:14][SH:15].C1(C=CC(O)=CC=1)O.[OH-].[Na+].[Cl-].[Na+]>CN(C)C=O>[C:1]([NH:3][C:4]([NH:7][CH2:8][C:9]#[CH:10])=[N:12][CH2:13][CH2:14][SH:15])#[N:2]

Participants

7

Reactant 5

HCID 785HydroquinoneHCID 5234Sodium ChlorideHCID 9082Cysteamine HydrochlorideHCID 14798Sodium HydroxideHCID 2805748Carbamimidothioic acid, N-cyano-N'-2-propynyl-, methyl ester

Product 1

HCID 136182246N-Cyano-N'-propargyl-N"-(2-mercaptoethyl)guanidine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of the product of Step A of Example 5 (1.53 g; 10 mmoles), cysteamine hydrochloride (1.136 g; 10 mmoles) and 0.055 g of hydroquinone in 10 ml of dimethylformamide is slightly warmed to dissolve. To this solution is added 10 ml of 1 N aqueous sodium hydroxide and nitrogen is bubbled through the solution. After standing at room temperature for 17 hours, the reaction mixture is evaporated to dryness to give a mixture of the title compound and sodium chloride. The title compound is extracted from the mixture with 10 ml of ethanol and the ethanolic solution is used in Step B below.

Workup

  1. temperatureis slightly warmed to dissolve
  2. customis bubbled through the solution
  3. customthe reaction mixture is evaporated to dryness
  4. customto give

Sources & evidence

ORD record
ord-f9d81d1b4cfc4966b3d434ca206e909c
Source dataset
uspto-grants-1981_08
Patent number
US04282363

Reaction notes

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