Acetonitrile → HCID 10379527, compound

HRID 1153964Notes

Reaction equation

HRID 1153964 reaction equation
[CH2:1]([C:3]1[N:4]([CH2:9][CH2:10][O:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[C:5](=[O:8])[NH:6][N:7]=1)[CH3:2].Cl[CH:19]([OH:22])[CH2:20][CH3:21].C(=O)([O-])[O-].[K+].[K+].C(#N)C>O>[OH:22][CH2:19][CH2:20][CH2:21][N:6]1[C:5](=[O:8])[N:4]([CH2:9][CH2:10][O:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[C:3]([CH2:1][CH3:2])=[N:7]1

Participants

6

Reactant 4

HCID 6342AcetonitrileHCID 11430Potassium CarbonateHCID 569735-Ethyl-4-(2-phenoxyethyl)-2,4-dihydro-3H-1,2,4-triazol-3-one2×HCID 151098631-Chloropropan-1-ol

Product 1

HCID 10379527HCID 10379527, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

The product of Example 5 "5-ethyl-4-(2-phenoxyethyl)-2H-1,2,4-triazol-3(4H)-one" (5.0 g., 23.5 mmol), chloropropanol (2.44 g., 25.8 mmol) and potassium carbonate (9.72 g., 70.4 mmol) in 50 ml. of acetonitrile is heated to reflux for a period of 48 hr. with stirring. Water (50 ml.) is added and the mixture extracted with methylene chloride which is dried over magnesium sulfate and concentrated under reduced pressure to afford 2-(3-hydroxypropyl)-5-ethyl-2,4-dihydro-4-(2-phenoxyethyl)-3H-1,2,4-triazol-3-one (XIV, Y=H, X1 =0, n=2, R2 =C2H5). Purification is carried out by flash chromatography with ethyl acetate.

Workup

  1. temperatureto reflux for a period of 48 hr
  2. extractionthe mixture extracted with methylene chloride which
  3. dry with materialis dried over magnesium sulfate
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-f4f3534b79e64bbb9fc7414f976697d2
Source dataset
uspto-grants-1984_12
Patent number
US04487773

Reaction notes

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