Hydrochloric Acid → 5-Carboxy-2-(4,5-dihydro-2-thiazolyl)-pyridine

HRID 1200023Notes

Reaction equation

HRID 1200023 reaction equation
[Na].[C:2]([C:5]1[CH:6]=[CH:7][C:8]([C:11]#[N:12])=[N:9][CH:10]=1)([OH:4])=[O:3].N[CH2:14][CH2:15][SH:16].Cl>O.C(O)C>[C:2]([C:5]1[CH:6]=[CH:7][C:8]([C:11]2[S:16][CH2:15][CH2:14][N:12]=2)=[N:9][CH:10]=1)([OH:4])=[O:3]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 6058CysteamineHCID 27611086-Cyanopyridine-3-carboxylic acidHCID 5360545Sodium2×

Product 1

HCID 198645865-Carboxy-2-(4,5-dihydro-2-thiazolyl)-pyridine

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

Sodium (11 mmol) is added to a flask containing 75 ml of ethanol. As soon as the sodium has dissolved, 10 mmol of 5-carboxy-2-cyanopyridine and 11 mmol of 2-amino-ethanethiol are added and the solution is refluxed for 24 h. The solution is then diluted with 25 ml of water, made acidic (pH=5) with 2N HCl and evaporated. The residue is dissolved in 100 ml of hot chloroform, the salts are filtered off and the filtrate on cooling gives crystals of the title compound, m.p. 234°-235° C.

Workup

  1. temperaturethe solution is refluxed for 24 h
  2. customevaporated
  3. dissolutionThe residue is dissolved in 100 ml of hot chloroform
  4. filtrationthe salts are filtered off
  5. temperaturethe filtrate on cooling

Sources & evidence

ORD record
ord-143d865299da42c986d2a696924ac583
Source dataset
uspto-grants-1990_02
Patent number
US04904675

Reaction notes

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