Cysteamine Hydrochloride → HCID 12943529, compound

HRID 1702244Notes

Reaction equation

HRID 1702244 reaction equation
Cl.[NH2:2][CH2:3][CH2:4][SH:5].[CH3:6][N:7]([CH2:9][C:10]1[O:14][C:13]([CH2:15]O)=[C:12]([CH3:17])[CH:11]=1)[CH3:8].[OH-].[K+]>Cl>[CH3:8][N:7]([CH2:9][C:10]1[O:14][C:13]([CH2:15][S:5][CH2:4][CH2:3][NH2:2])=[C:12]([CH3:17])[CH:11]=1)[CH3:6]

Participants

5

Reactant 3

HCID 9082Cysteamine HydrochlorideHCID 14797Potassium HydroxideHCID 13102904HCID 13102904, compound

Product 1

HCID 12943529HCID 12943529, compoundYield 91.1%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

To a solution of 2-aminoethanethiol hydrochloride (2.27 g; 20.0 mmoles) in 20 ml of concentrated HCl that was cooled in an ice-salt bath to -10° was added dropwise 5-dimethylaminomethyl-3-methyl-2-furanmethanol (3.38 g; 20.0 mmoles) [prepared in Step A], and the mixture stirred for 15 minutes then allowed to stand in the cold (0°) overnight. After 17 hours the cold solution was made strongly basic with aqueous KOH solution and then extracted with five portions of methylene chloride. The combined organic phase was dried, filtered and evaporated under reduced pressure to yield the title compound (4.16 g), bp 110°-120°/0.1 mm Hg.

Workup

  1. customto stand in the cold (0°) overnight
  2. extractionextracted with five portions of methylene chloride
  3. customThe combined organic phase was dried
  4. filtrationfiltered
  5. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-751f5aeb7e2641c28ba208dbdef3e249
Source dataset
uspto-grants-1983_04
Patent number
US04380638

Reaction notes

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