Ethanol → HCID 136144789, compound

HRID 638030Notes

Reaction equation

HRID 638030 reaction equation
O.O.[OH:3][C:4]1[CH:12]=[CH:11][C:7]([C:8]([NH2:10])=[NH:9])=[CH:6][CH:5]=1.C(O)C.[F:16][C:17]([F:25])([F:24])[C:18]([CH2:20][C:21](=O)[CH3:22])=O>CCOCC>[OH:3][C:4]1[CH:12]=[CH:11][C:7]([C:8]2[N:10]=[C:21]([CH3:22])[CH:20]=[C:18]([C:17]([F:25])([F:24])[F:16])[N:9]=2)=[CH:6][CH:5]=1

Participants

5

Reactant 3

HCID 702EthanolHCID 739431,1,1-Trifluoro-2,4-pentanedioneHCID 136387284HCID 136387284, compound

Product 1

HCID 136144789HCID 136144789, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

In a pressure tube a mixture of 17.2 g of 4-hydroxybenzamidine dihydrate, 60 ml of ethanol and 14.6 ml of trifluoroacetylacetone is heated for 18 hours at a bath temperature of 110°. The mixture is then stirred with 200 ml of ether, a small amount of precipitate is filtered off with suction and the filtrate is extracted with two portions of 2N sodium hydroxide solution. The alkaline solution is treated with carbon, filtered and then 400 ml of ethyl acetate and 160 ml of 2N hydrochloric acid are added to pH 1. The organic phase is separated off, washed with water, dried over sodium sulphate and concentrated by evaporation. The residue is recrystallised from ether/hexane yielding 2-(4-hydroxyphenyl)-4-methyl-6-(trifluoromethyl)-pyrimidine having a melting point of 131°-132° C.

Workup

  1. temperatureis heated for 18 hours at a bath temperature of 110°
  2. filtrationa small amount of precipitate is filtered off with suction
  3. extractionthe filtrate is extracted with two portions of 2N sodium hydroxide solution
  4. additionThe alkaline solution is treated with carbon
  5. filtrationfiltered
  6. addition400 ml of ethyl acetate and 160 ml of 2N hydrochloric acid are added to pH 1
  7. customThe organic phase is separated off
  8. washwashed with water
  9. dry with materialdried over sodium sulphate
  10. concentrationconcentrated by evaporation
  11. customThe residue is recrystallised from ether/hexane

Sources & evidence

ORD record
ord-ff6cdb42c929498b8f2a8b85e8990566
Source dataset
uspto-grants-1985_12
Patent number
US04559354

Reaction notes

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