Hydrochloric Acid → [4-Chloro-6-(2,3-xylidino)-2-pyrimidinylthio]acetic acid

HRID 1578943Notes

Reaction equation

HRID 1578943 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.[CH3:16][C:17]1[C:23]([CH3:24])=[CH:22][CH:21]=[CH:20][C:18]=1[NH2:19].C(=O)([O-])[O-].[Na+].[Na+].Cl>C(O)C>[Cl:13][C:11]1[CH:10]=[C:9]([NH:19][C:18]2[CH:20]=[CH:21][CH:22]=[C:23]([CH3:24])[C:17]=2[CH3:16])[N:8]=[C:7]([S:6][CH2:5][C:4]([OH:3])=[O:15])[N:12]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 68932,3-DimethylanilineHCID 10340Sodium CarbonateHCID 4133103Acetic acid, [(4,6-dichloro-2-pyrimidinyl)thio]-, ethyl ester

Product 1

HCID 5694[4-Chloro-6-(2,3-xylidino)-2-pyrimidinylthio]acetic acid

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 21.4 g of (4,6-dichloro-2-pyrimidinylthio) acetic acid ethyl ester, 9.7 g of 2,3-dimethylaniline, 8.5 g of anhydrous sodium carbonate in 200 ml. of ethanol was heated under reflux with stirring for 4 hr. The mixture was filtered and water was added to the filtrate until precipitation occurred. This material was removed by filtration and amounted to 7.0 g. This material was treated with boiling 30% sodium hydroxide solution (30 ml.) and sufficient ethanol to obtain a clear solution. After cooling in ice the material was acidified with 30% hydrochloric acid solution. The resulting product was then recrystallized from ethanol giving 4.3 g of product, mp. 146°-151°C.

Workup

  1. temperatureunder reflux
  2. filtrationThe mixture was filtered
  3. additionwater was added to the filtrate until precipitation
  4. customThis material was removed by filtration
  5. additionThis material was treated
  6. customto obtain a clear solution
  7. temperatureAfter cooling in ice the material
  8. customThe resulting product was then recrystallized from ethanol giving 4.3 g of product, mp. 146°-151°C.

Sources & evidence

ORD record
ord-fe666b0ebdcd4edf8545d6c0d0bb7c21
Source dataset
uspto-grants-1976_02
Patent number
US03940394

Reaction notes

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