3-Pyridinecarboxaldehyde → 3-[5-(4-Chlorophenyl)-2,3-dihydro-1,3,4-thiadiazol-2-yl]pyridine

HRID 255892Notes

Reaction equation

HRID 255892 reaction equation
[Cl:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([NH:8][NH2:9])=[S:7])=[CH:4][CH:3]=1.[N:12]1[CH:17]=[CH:16][CH:15]=[C:14]([CH:18]=O)[CH:13]=1>C(O)C>[Cl:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]2[S:7][CH:18]([C:14]3[CH:13]=[N:12][CH:17]=[CH:16][CH:15]=3)[NH:9][N:8]=2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 103713-PyridinecarboxaldehydeHCID 124770754-Chloro-thiobenzoic acid hydrazide

Product 1

HCID 157083633-[5-(4-Chlorophenyl)-2,3-dihydro-1,3,4-thiadiazol-2-yl]pyridine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

39.2 g of p-chlorothiobenzoic acid hydrazide are dissolved in 350 ml of ethanol. Under nitrogen, 21.4 g of pyridine-3-aldehyde (dissolved in 20 ml of ethanol) are added dropwise to this solution. The reaction temperature is kept at 20° C. by cooling. When the addition is complete, the reaction mixture is stirred for 1 hour at reflux temperature and subsequently filtered through finely particulate diatomaceous earth. The filtrate is concentrated to three quarters of its initial volume and the precipitated product is isolated by filtration, washed with hexane and dried, affording the title compound of the formula ##STR8## with a melting point of 106°-108° C. (compound 1.1).

Workup

  1. customis kept at 20° C.
  2. temperatureby cooling
  3. additionWhen the addition
  4. temperatureat reflux temperature
  5. filtrationsubsequently filtered through finely particulate diatomaceous earth
  6. concentrationThe filtrate is concentrated to three quarters of its initial volume
  7. customthe precipitated product is isolated by filtration
  8. washwashed with hexane
  9. customdried

Sources & evidence

ORD record
ord-1be53cd740d54dbea094fc9e3c17a57f
Source dataset
uspto-grants-1987_10
Patent number
US04699913

Reaction notes

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