Cysteamine Hydrochloride → HCID 178512682, compound

HRID 1980717Notes

Reaction equation

HRID 1980717 reaction equation
Cl.[NH2:2][CH2:3][CH2:4][SH:5].[NH:6]([C:10]1[S:11][C:12]([CH2:15]O)=[CH:13][N:14]=1)[C:7]([NH2:9])=[NH:8].[OH-].[Na+]>Cl>[NH:6]([C:10]1[S:11][C:12]([CH2:15][S:5][CH2:4][CH2:3][NH2:2])=[CH:13][N:14]=1)[C:7]([NH2:9])=[NH:8]

Participants

5

Reactant 3

HCID 9082Cysteamine HydrochlorideHCID 14798Sodium HydroxideHCID 178512681HCID 178512681, compound

Product 1

HCID 178512682HCID 178512682, compoundYield 697.2%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

Cysteamine hydrochloride (10.6 g; 9.3 mmoles) and 2-guanidino-5-hydroxymethylthiazole (16.0 g; 9.3 mmoles) [prepared in Step B] were dissolved in 80 ml of concentrated hydrochloric acid and the solution stirred at ambient temperature for 1 hour and then heated at reflux temperature for 3 hours. The reaction mixture was cooled, made basic (pH 11) with 40% aqueous NaOH and filtered to give 15 g of product. Recrystallization from acetonitrile yielded the title compound, mp 150°-153°.

Workup

  1. temperatureheated
  2. temperatureat reflux temperature for 3 hours
  3. temperatureThe reaction mixture was cooled
  4. filtrationfiltered

Sources & evidence

ORD record
ord-793d0b68a5294b6eb9b9fabf25fb9363
Source dataset
uspto-grants-1985_04
Patent number
US04510309

Reaction notes

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