Hydrochloric Acid → [4-Chloro-6-(p-chlorobenzylamino)-2-pyrimidinylthio]acetic acid

HRID 1578951Notes

Reaction equation

HRID 1578951 reaction equation
C([O:3][C:4](=[O:23])[CH2:5][S:6][C:7]1[N:12]=[C:11]([Cl:13])[CH:10]=[C:9]([NH:14][CH2:15][C:16]2[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][CH:17]=2)[N:8]=1)C.[OH-].[Na+].Cl>>[Cl:13][C:11]1[CH:10]=[C:9]([NH:14][CH2:15][C:16]2[CH:17]=[CH:18][C:19]([Cl:22])=[CH:20][CH:21]=2)[N:8]=[C:7]([S:6][CH2:5][C:4]([OH:23])=[O:3])[N:12]=1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 53738869[4-Chloro-6-(p-chlorobenzylamino)-2-pyrimidinylthio]acetic acid ethyl ester

Product 1

HCID 21557346[4-Chloro-6-(p-chlorobenzylamino)-2-pyrimidinylthio]acetic acidYield 77.2%

Procedure

[4-Chloro-6-(p-chlorobenzylamino)-2-pyrimidinylthio]acetic acid ethyl ester (1.4 g) was heated for 5 minutes with 30 ml. of 30% sodium hydroxide solution on a hot plate. The reaction mixture was then cooled and acidified with concentrated hydrochloric acid solution. The resulting precipitate was removed by filtration, washed with water and recrystallized from ethanol to afford 1.0 g of product, mp. 211°-213°C., decomp.

Workup

  1. temperatureThe reaction mixture was then cooled
  2. customThe resulting precipitate was removed by filtration
  3. washwashed with water
  4. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-8299649113584450b6e0e09d62ef5c0f
Source dataset
uspto-grants-1976_02
Patent number
US03940394

Reaction notes

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