1-Butanol → HCID 54022774, compound

HRID 232904Notes

Reaction equation

HRID 232904 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([C:8](Cl)=[O:9])[CH:5]=[CH:4][N:3]=1.C([O-])(O)=O.[Na+].[CH2:16]([OH:20])[CH2:17][CH2:18][CH3:19]>>[CH2:16]([O:20][C:8]([C:6]1[CH:5]=[CH:4][N:3]=[C:2]([Cl:1])[N:7]=1)=[O:9])[CH2:17][CH2:18][CH3:19]

Participants

4

Reactant 3

HCID 2631-ButanolHCID 516892Sodium BicarbonateHCID 450814902-Chloropyrimidine-4-carbonyl chloride

Product 1

HCID 54022774HCID 54022774, compoundYield 85%

Procedure

A solution of 0.52 g (2.93 mmol) of 2-chloropyrimidine-4-carboxylic acid chloride in 10 ml of butanol was stirred for 1.5 hours at room temperature. Then the reaction solution was poured on 80 ml of NaHCO3 solution and extracted three times with 60 ml of ethyl acetate each. The combined organic phase was washed with 60 ml of saturated NaCl solution, dried on Na2SO4 and concentrated by evaporation on a rotary evaporator. After drying of the product on a high vacuum, 0.53 g of product was obtained as a white solid, corresponding to a yield of 85 percent relative to the 2-chloropyrimidine-4-carboxylic acid chloride used. The melting point of the product was 67.9° to 68.8° C. Other data for the product was:

Workup

  1. extractionextracted three times with 60 ml of ethyl acetate each
  2. washThe combined organic phase was washed with 60 ml of saturated NaCl solution
  3. customdried on Na2SO4
  4. concentrationconcentrated by evaporation on a rotary evaporator
  5. customAfter drying of the product on a high vacuum

Sources & evidence

ORD record
ord-1ba3b301b7e64894b722a0bdc0f9c004
Source dataset
uspto-grants-1997_01
Patent number
US05591853

Reaction notes

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