Cysteamine Hydrochloride → 4-[[(2-Aminoethyl)thio]-methyl]-2-hydroxymethylthiazole

HRID 1736660Notes

Reaction equation

HRID 1736660 reaction equation
[OH-].[K+].Cl.[NH2:4][CH2:5][CH2:6][SH:7].Cl.Cl[CH2:10][C:11]1[N:12]=[C:13]([CH2:16][OH:17])[S:14][CH:15]=1>C(O)(C)C>[NH2:4][CH2:5][CH2:6][S:7][CH2:10][C:11]1[N:12]=[C:13]([CH2:16][OH:17])[S:14][CH:15]=1

Participants

5

Reactant 3

HCID 9082Cysteamine HydrochlorideHCID 14797Potassium HydroxideHCID 21464457[4-(Chloromethyl)-1,3-thiazol-2-yl]methanol hydrochloride

Product 1

HCID 196122374-[[(2-Aminoethyl)thio]-methyl]-2-hydroxymethylthiazole

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

Potassium hydroxide (10.6 g) was added to a suspension of 6.82 g of cysteamine hydrochloride and 10.0 g of 4-chloromethyl-2-hydroxymethylthiazole hydrochloride in 100 ml isopropanol. The resulting suspension was stirred an room temperature for 2 hours and filtered through a pad of celite to remove insoluble inorganics and concentrated under reduced pressure. The residue was taken up in dichloromethane and filtered through a pad of celite and concentrated under reduced pressure. The oil (12.54 g) represents a quantitative yield of 4-[[(2-aminoethyl)thio]methyl]-2-hydroxymethylthiazole contaminated only with inorganic salts.

Workup

  1. filtrationfiltered through a pad of celite
  2. customto remove insoluble inorganics
  3. concentrationconcentrated under reduced pressure
  4. filtrationfiltered through a pad of celite
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-0781977b02374eecbe8f381c868e9824
Source dataset
uspto-grants-1996_07
Patent number
US05541335

Reaction notes

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