Hydrochloric Acid → HCID 19910254, compound

HRID 1578953Notes

Reaction equation

HRID 1578953 reaction equation
C([O:3][C:4](=[O:16])[CH:5]([S:7][C:8]1[N:13]=[C:12]([Cl:14])[CH:11]=[C:10](Cl)[N:9]=1)[CH3:6])C.[Cl:17][C:18]1[CH:25]=[CH:24][C:21]([CH2:22][NH2:23])=[CH:20][CH:19]=1.C(=O)([O-])[O-].[Na+].[Na+].Cl>C(O)C>[Cl:14][C:12]1[CH:11]=[C:10]([NH:23][CH2:22][C:21]2[CH:24]=[CH:25][C:18]([Cl:17])=[CH:19][CH:20]=2)[N:9]=[C:8]([S:7][CH:5]([CH3:6])[C:4]([OH:3])=[O:16])[N:13]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 10340Sodium CarbonateHCID 660364-ChlorobenzylamineHCID 53993127HCID 53993127, compound

Product 1

HCID 19910254HCID 19910254, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A stirred mixture of 5.6 g of 2-(4,6-dichloro-2-pyrimidinylthio) propionic acid ethyl ester, 2.9 g of p-chlorobenzylamine and 2.1 g of anhydrous sodium carbonate in 50 ml. of ethanol were heated under reflux for 6 hr. The reaction mixture was filtered and taken to dryness on a rotary evaporator. The residue was dissolved in ether and filtered free of insoluble material. The ether was removed on a rotary evaporator and the residue was treated with approximately 10 ml. of 30% sodium hydroxide solution to which was added enough ethanol until a clear solution was obtained. The reaction mixture was heated on a steam bath for a few minutes then acidified with concentrated hydrochloric acid solution. The precipitate which was formed was recrystallized from 95% ethanol affording 5.0 g of product, mp. 133°-136°C.

Workup

  1. temperatureunder reflux for 6 hr
  2. filtrationThe reaction mixture was filtered
  3. customtaken to dryness on a rotary evaporator
  4. dissolutionThe residue was dissolved in ether
  5. filtrationfiltered free of insoluble material
  6. customThe ether was removed on a rotary evaporator
  7. additionthe residue was treated with approximately 10 ml
  8. additionof 30% sodium hydroxide solution to which was added enough ethanol until a clear solution
  9. customwas obtained
  10. temperatureThe reaction mixture was heated on a steam bath for a few minutes
  11. customThe precipitate which was formed
  12. customwas recrystallized from 95% ethanol affording 5.0 g of product, mp. 133°-136°C.

Sources & evidence

ORD record
ord-fc4242677f454014a8387d0436feba00
Source dataset
uspto-grants-1976_02
Patent number
US03940394

Reaction notes

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