Ethanol → HCID 178485018, compound

HRID 838858Notes

Reaction equation

HRID 838858 reaction equation
Cl.[NH2:2][CH2:3][CH2:4][SH:5].[C:6]([N:8](C)[C:9](=[NH:12])SC)#[N:7].[OH-].[Na+].[CH2:16](O)C>O>[C:6]([NH:8][C:9]([NH:12][CH3:16])=[N:2][CH2:3][CH2:4][SH:5])#[N:7]

Participants

6

Reactant 4

HCID 702EthanolHCID 9082Cysteamine HydrochlorideHCID 14798Sodium HydroxideHCID 21660514N-cyano-N,S-dimethyl-isothiourea

Product 1

HCID 178485018HCID 178485018, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

A solution of cysteamine hydrochloride (5.68 g) in water (20 ml) was added to a suspension of N-cyano-N,S-dimethylisothiourea (6.46 g) in ethanol (100 ml). A solution of sodium hydroxide (4.0 g) in water (20 ml) was added to the mixture and the suspension was heated under reflux for one hour. The resulting clear solution was concentrated to remove ethanol, a little more water was added and the alkaline aqueous solution was extracted with ethyl acetate. The aqueous solution was adjusted to pH4 with hydrochloric acid and extracted with ethyl acetate. This latter organic extract was dried and evaporated to give N-cyano-N'-methyl-N"-(2-mercaptoethyl)guanidine (6.12 g) as a colourless oil.

Workup

  1. temperaturethe suspension was heated
  2. temperatureunder reflux for one hour
  3. concentrationThe resulting clear solution was concentrated
  4. customto remove ethanol
  5. additiona little more water was added
  6. extractionthe alkaline aqueous solution was extracted with ethyl acetate
  7. extractionextracted with ethyl acetate
  8. extractionThis latter organic extract
  9. customwas dried
  10. customevaporated

Sources & evidence

ORD record
ord-ae6491e4d3524d3299140aa4dfdc8efc
Source dataset
uspto-grants-1978_06
Patent number
US04093621

Reaction notes

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