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

HRID 236852Notes

Reaction equation

HRID 236852 reaction equation
Cl.[NH2:2][CH2:3][CH2:4][SH:5].[C:6]([NH:8][C:9](=[N:12][CH2:13][C:14]#[CH:15])SC)#[N:7].C1(C=CC(O)=CC=1)O.[OH-].[Na+].[Cl-].[Na+]>CN(C=O)C>[C:6]([NH:8][C:9]([NH:12][CH2:13][C:14]#[CH:15])=[N:2][CH2:3][CH2:4][SH:5])#[N:7]

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 1.136 g (10 m moles) of cysteamine hydrochloride, 1.53 g (10 m moles) of the product of step A, above, and 0.055 g of hydroquinone in 10 ml DMF was slightly warmed to dissolve. To this solution was added 10 ml of 1 N aqueous sodium hydroxide and nitrogen was bubbled through the solution. After standing at room temperature for 17 hours, the reaction mixture was evaporated to dryness to give a mixture of the title product and sodium chloride. The title product was extracted from this mixture with 10 ml of ethanol and the ethanolic solution was used in step C, below.

Workup

  1. customwas bubbled through the solution
  2. customthe reaction mixture was evaporated to dryness
  3. customto give

Sources & evidence

ORD record
ord-91ce134a81e54826a4aa40efdcf8d199
Source dataset
uspto-grants-1979_06
Patent number
US04158013

Reaction notes

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