Cysteamine → 2-(2-Chloro-5-pyridyl)thiazolidine

HRID 377000Notes

Reaction equation

HRID 377000 reaction equation
[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=O)=[CH:4][N:3]=1.[NH2:10][CH2:11][CH2:12][SH:13]>C1C=CC=CC=1>[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]2[NH:10][CH2:11][CH2:12][S:13]2)=[CH:4][N:3]=1

Participants

4

Reactant 2

HCID 6058CysteamineHCID 27640536-Chloropyridine-3-carbaldehyde

Product 1

HCID 137527892-(2-Chloro-5-pyridyl)thiazolidineYield 89.9%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A solution composed of 6-chloronicotinaldehyde (14.2 g), 2-aminoethanethiol (7.7 g) and benzene (80 ml) was heated with stirring for 5 hours while removing water as an azeotrope. After the reaction, benzene was distilled off under reduced pressure, and further volatile materials were removed at 1 mmHg and 70° C. to give 2-(2-chloro-5-pyridyl)thiazolidine (18 g) as a residue. Ten grams of 2-(2-chloro-5-pyridyl)thiazolidine was dissolved in 100 ml of ethanol, and sodium borohydride was added. With stirring, the mixture was gradually heated and thereafter re-fluxed for 1 hour. Ethanol was distilled off under reduced pressure, and chloroform was added to the residue. Insoluble materials were separated by filtration and the chloroform layer was washed with water and dehydrated. Chloroform was distilled off under reduced pressure to give the desired N-(2-chloro-5-pyridylmethyl)2-aminoethanethiol (8.3 g).

Workup

  1. temperaturewas heated
  2. customwhile removing water as an azeotrope
  3. customAfter the reaction, benzene
  4. distillationwas distilled off under reduced pressure, and further volatile materials
  5. customwere removed at 1 mmHg and 70° C.

Sources & evidence

ORD record
ord-0c47dd5a83c541e1bc869161d7f9d9bf
Source dataset
uspto-grants-2000_02
Patent number
US06022967

Reaction notes

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