Acetic Acid → HCID 13390402, compound

HRID 1979918Notes

Reaction equation

HRID 1979918 reaction equation
C(O[C:4](=[NH:22])[CH2:5][C:6]([C:14]1[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][C:15]=1[Cl:21])([OH:13])[CH2:7][N:8]1[CH:12]=[N:11][CH:10]=[N:9]1)C.C(O[CH:26](OCC)[CH2:27][NH2:28])C.C(O)(=O)C.Cl>O1CCCC1.C(=O)([O-])[O-].[Na+].[Na+].C(OCC)C>[Cl:21][C:15]1[CH:16]=[C:17]([Cl:20])[CH:18]=[CH:19][C:14]=1[C:6]([OH:13])([CH2:7][N:8]1[CH:12]=[N:11][CH:10]=[N:9]1)[CH2:5][C:4]1[NH:22][CH:26]=[CH:27][N:28]=1

Participants

8

Reactant 4

HCID 176Acetic AcidHCID 313Hydrochloric AcidHCID 695242,2-DiethoxyethylamineHCID 13390397HCID 13390397, compound

Product 1

HCID 13390402HCID 13390402, compound

Reagents, catalysts & solvents 3

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolventHCID 10340Sodium CarbonateSolvent

Conditions

Temperature
70 °C

Procedure

A solution of 3-(2,4-dichlorophenyl)-3-hydroxy-4-(1H-1,2,4-triazol-1-yl)butyrimidic acid ethyl ester free base (546 mg), aminoacetaldehyde diethylacetal (234 mg) and acetic acid (210 mg) in tetrahydrofuran (4 ml) was heated under reflux for 2 hours. Hydrochloric acid (4 ml, 5N) was added and the mixture heated to 70° C. for 30 minutes. The mixture was diluted with saturated sodium carbonate to pH8 and extracted with ethyl acetate (3×20 ml). The organic extracts were dried over magnesium sulphate and evaporated to yield a gum which was chromatographed on silica eluting with a mixture of methylene chloride, isopropanol and concentrated ammonium hydroxide (85:15:1 by volume). Fractions containing the desired product were pooled and evaporated to yield a gum which solidified on trituration with diethyl ether (246 mg). Recrystallisation from isopropanol gave the title compound as colourless crystals m.p. 168°-170° C. Found: C,49.8; H,3.9; N,20.9. C14H13Cl2N5O requires C,49.7; H,3.9; N,20.7%.

Workup

  1. temperatureunder reflux for 2 hours
  2. extractionextracted with ethyl acetate (3×20 ml)
  3. dry with materialThe organic extracts were dried over magnesium sulphate
  4. customevaporated
  5. customto yield a gum which
  6. customwas chromatographed on silica eluting with a mixture of methylene chloride, isopropanol and concentrated ammonium hydroxide (85:15:1 by volume)
  7. additionFractions containing the desired product
  8. customevaporated
  9. customto yield a gum which
  10. customRecrystallisation from isopropanol

Sources & evidence

ORD record
ord-27ae66be117444c1ae20a6cafe55661c
Source dataset
uspto-grants-1984_11
Patent number
US04483863

Reaction notes

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