Sodium Carbonate → HCID 21557352, compound

HRID 1578949Notes

Reaction equation

HRID 1578949 reaction equation
C([O:3][C:4](=[O:15])[CH2:5][S:6][C:7]1[N:12]=[C:11]([Cl:13])[CH:10]=[C:9](Cl)[N:8]=1)C.[Cl:16][C:17]1[CH:25]=[CH:24][C:20]([CH:21]([NH2:23])[CH3:22])=[CH:19][CH:18]=1.C(=O)([O-])[O-].[Na+].[Na+]>C(O)C>[Cl:13][C:11]1[CH:10]=[C:9]([NH:23][CH:21]([CH3:22])[C:20]2[CH:24]=[CH:25][C:17]([Cl:16])=[CH:18][CH:19]=2)[N:8]=[C:7]([S:6][CH2:5][C:4]([OH:3])=[O:15])[N:12]=1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 978031-(4-Chlorophenyl)ethylamineHCID 4133103Acetic acid, [(4,6-dichloro-2-pyrimidinyl)thio]-, ethyl ester

Product 1

HCID 21557352HCID 21557352, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A stirred mixture of 2.7 g of (4,6-dichloro-2-pyrimidinylthio)acetic acid ethyl ester, 1.6 g of p-chloro-α-methylbenzylamine and 1.1 g of sodium carbonate in 120 ml. ethanol was heated under reflux for 2 hr. The reaction mixture was filtered and the filtrate taken to dryness in a rotary evaporator in vacuo. The residual oil was treated with 100 ml. of 30% sodium hydroxide solution containing a few ml. of ethanol. After a few minutes the clear solution was acidified with concentrated hydrochloric acid and the mixture thus formed was extracted with ether (3 × 50 ml.). The ether solution was dried over magnesium sulfate, filtered and the filtrate evaporated to dryness. The residue was dissolved in 50 ml. of benzene and petroleum ether was added until the solution became cloudy. On cooling in ice a precipitate was deposited. Recrystallization of this material from 50% aqueous ethanol afforded the product, mp. 155°-160°C.

Workup

  1. temperatureunder reflux for 2 hr
  2. filtrationThe reaction mixture was filtered
  3. customthe filtrate taken to dryness in a rotary evaporator in vacuo
  4. additionThe residual oil was treated with 100 ml
  5. additionof 30% sodium hydroxide solution containing a few ml
  6. waitAfter a few minutes the clear solution was acidified with concentrated hydrochloric acid
  7. customthe mixture thus formed
  8. extractionwas extracted with ether (3 × 50 ml.)
  9. dry with materialThe ether solution was dried over magnesium sulfate
  10. filtrationfiltered
  11. customthe filtrate evaporated to dryness
  12. dissolutionThe residue was dissolved in 50 ml
  13. additionof benzene and petroleum ether was added until the solution
  14. temperatureOn cooling in ice a precipitate
  15. customRecrystallization of this material from 50% aqueous ethanol
  16. customafforded the product, mp. 155°-160°C.

Sources & evidence

ORD record
ord-593c67aebe6241dab4a5c93c8860d200
Source dataset
uspto-grants-1976_02
Patent number
US03940394

Reaction notes

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