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

HRID 1290118Notes

Reaction equation

HRID 1290118 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 refluxed 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-80963c3f14a245cc9907e69809da5e82
Source dataset
uspto-grants-1998_05
Patent number
US05750704

Reaction notes

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