Hydrochloric Acid → HCID 20271354, compound

HRID 485069Notes

Reaction equation

HRID 485069 reaction equation
[OH:1][CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[NH:13][N:12]=[C:11]([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([O:20][CH2:21][CH3:22])[CH:15]=2)[N:10]=1.[C:23](Cl)(=[O:31])[CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH3:30].C([O-])(O)=O.[Na+].Cl.C([O-])([O-])=O.[K+].[K+]>ClCCCl.O.CO.C1(C)C=CC=CC=1.C(OCC)(=O)C>[CH2:21]([O:20][C:16]1[CH:15]=[C:14]([C:11]2[N:10]=[C:9]([C:4]3[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=3[CH2:2][O:1][C:23](=[O:31])[CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH3:30])[NH:13][N:12]=2)[CH:19]=[CH:18][CH:17]=1)[CH3:22]

Participants

10

Reactant 5

HCID 313Hydrochloric AcidHCID 8124Octanoyl chlorideHCID 11430Potassium CarbonateHCID 516892Sodium BicarbonateHCID 22251273HCID 22251273, compound

Product 1

HCID 20271354HCID 20271354, compoundYield 61%

Reagents, catalysts & solvents 4

HCID 111,2-DichloroethaneSolventHCID 887MethanolSolventHCID 962WaterSolventHCID 21584019Toluene ethylacetateSolvent

Procedure

A mixture of 5-(2-hydroxymethylphenyl)-3-(3-ethoxyphenyl)-1H-1,2,4-triazole (2.36 g, 8 mmole) and octanoyl chloride (1.6 ml, 9.4 mmole) in 1,2-dichloroethane (24 ml) is heated to the reflux temperature with stirring. When the reaction, which is followed by thin layer chromatography (silica-gel plates, toluene: ethyl acetate 1:1), is complete, the reaction mixture is cooled to room temperature and methanol (8 ml) is added. Then an excess of NaHCO3 (1.21 g, 14.4 mmole) is added to neutralize the hydrochloric acid formed during the reaction, followed, after a few minutes, by anhydrous K2CO3 (0.062 g, 0.45 mmole). When the partial transesterification of the N,O-diacyl derivative into the desired monoacyloxy one is complete, the reaction mixture is diluted with water (20 ml), the organic phase is separated and the aqueous one is extracted with methylene chloride (2×10 ml). The organic extracts are combined, washed with water, dried over Na2SO4 and concentrated to dryness giving a row residue which is purified by crystallization from hexane. Yield: 61%. M.p. 87°-89° C.

Workup

  1. temperatureis heated to the reflux temperature
  2. customWhen the reaction, which
  3. customformed during the reaction
  4. customthe organic phase is separated
  5. extractionthe aqueous one is extracted with methylene chloride (2×10 ml)
  6. washwashed with water
  7. dry with materialdried over Na2SO4
  8. concentrationconcentrated to dryness
  9. customgiving a row residue which
  10. customis purified by crystallization from hexane

Sources & evidence

ORD record
ord-7e99c78f56ff4b35b518c044b912d8e3
Source dataset
uspto-grants-1985_08
Patent number
US04535090

Reaction notes

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