Methanol → HCID 21557354, compound

HRID 1578956Notes

Reaction equation

HRID 1578956 reaction equation
[Na].C([O:4][C:5](=[O:21])[CH2:6][S:7][C:8]1[N:13]=[C:12](Cl)[CH:11]=[C:10]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[N:9]=1)C.[CH3:22][OH:23]>>[CH3:22][O:23][C:12]1[CH:11]=[C:10]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[N:9]=[C:8]([S:7][CH2:6][C:5]([OH:4])=[O:21])[N:13]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 5360545SodiumHCID 54085186HCID 54085186, compound

Product 1

HCID 21557354HCID 21557354, compound

Procedure

To a solution of 0.46 g of sodium metal in 50 ml. of absolute methanol was added 3.2 g of (4-chloro-6-phenyl-2-pyrimidinylthio)acetic acid ethyl ester as prepared in the preceding Example. The reaction mixture was heated under reflux for 3 hr. then filtered. The filtrate was taken to dryness in a rotary evaporator. The residue was dissolved in 30 ml. of 50% sodium hydroxide and the solution was diluted to 200 ml. The reaction mixture was allowed to stand at room temperature for 1.5 hr, cooled in ice and acidified with concentrated hydrochloric acid. The resulting precipitate was recrystallized from aqueous ethanol affording 1.4 g of product, mp. 157°-159°C.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureunder reflux for 3 hr
  3. filtrationthen filtered
  4. customThe filtrate was taken to dryness in a rotary evaporator
  5. dissolutionThe residue was dissolved in 30 ml
  6. additionof 50% sodium hydroxide and the solution was diluted to 200 ml
  7. temperaturecooled in ice
  8. customThe resulting precipitate was recrystallized from aqueous ethanol affording 1.4 g of product, mp. 157°-159°C.

Sources & evidence

ORD record
ord-4c2f40ac956d4554895e7c7b5acf0e14
Source dataset
uspto-grants-1976_02
Patent number
US03940394

Reaction notes

Loading…