Sodium Carbonate → HCID 53909308, compound

HRID 1578958Notes

Reaction equation

HRID 1578958 reaction equation
Cl[C:2]1[CH:7]=[CH:6][N:5]=[C:4]([S:8][CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])[N:3]=1.[Cl:15][C:16]1[CH:23]=[CH:22][C:19]([CH2:20][NH2:21])=[CH:18][CH:17]=1.C(=O)([O-])[O-].[Na+].[Na+]>C(O)C>[CH2:13]([O:12][C:10](=[O:11])[CH2:9][S:8][C:4]1[N:3]=[C:2]([NH:21][CH2:20][C:19]2[CH:22]=[CH:23][C:16]([Cl:15])=[CH:17][CH:18]=2)[CH:7]=[CH:6][N:5]=1)[CH3:14]

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 660364-ChlorobenzylamineHCID 12054386HCID 12054386, compound

Product 1

HCID 53909308HCID 53909308, compoundYield 38.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A stirred mixture of 10.0 g of (4-chloro-2-pyrimidinylthio)acetic acid, ethyl ester, 6.0 g of p-chlorobenzylamine and 4.5 g of sodium carbonate in 150 ml. of ethanol was heated under reflux for 5 hr. The reaction mixture was filtered and water was added to the filtrate to induce crystallization. After cooling in ice the precipitate was collected on a filter. Recrystallization from benzene-petroleum ether afforded 5.5 g of product, mp. 175-178°C.

Workup

  1. temperatureunder reflux for 5 hr
  2. filtrationThe reaction mixture was filtered
  3. additionwater was added to the filtrate
  4. customcrystallization
  5. temperatureAfter cooling in ice the precipitate
  6. customwas collected on a filter
  7. customRecrystallization from benzene-petroleum ether

Sources & evidence

ORD record
ord-1082b9dd1a19429b840a2fe93897daf0
Source dataset
uspto-grants-1976_02
Patent number
US03940394

Reaction notes

Loading…