Pyridine → 3-(N-Acetylcarbamoyl)-2-(2,4-dichlorophenyl)-1-(1H-1,2,4-triazol-1-yl)propan-2-ol hemihydrate

HRID 2164282Notes

Reaction equation

HRID 2164282 reaction equation
[C:1](Cl)(=[O:3])[CH3:2].[C:5]([CH2:8][C:9]([C:17]1[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][C:18]=1[Cl:24])([OH:16])[CH2:10][N:11]1[CH:15]=[N:14][CH:13]=[N:12]1)(=[O:7])[NH2:6].N1C=CC=CC=1>C(#N)C>[OH2:3].[C:1]([NH:6][C:5]([CH2:8][C:9]([C:17]1[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][C:18]=1[Cl:24])([OH:16])[CH2:10][N:11]1[CH:15]=[N:14][CH:13]=[N:12]1)=[O:7])(=[O:3])[CH3:2].[C:1]([NH:6][C:5]([CH2:8][C:9]([C:17]1[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][C:18]=1[Cl:24])([OH:16])[CH2:10][N:11]1[CH:15]=[N:14][CH:13]=[N:12]1)=[O:7])(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 1049PyridineHCID 6367Acetyl chlorideHCID 136030731-Carbamoyl-2-(2,4-dichlorophenyl)-3-(1H-1,2,4-triazol-1-yl)propan-2-ol

Product 1

HCID 704255333-(N-Acetylcarbamoyl)-2-(2,4-dichlorophenyl)-1-(1H-1,2,4-triazol-1-yl)propan-2-ol hemihydrateYield 19%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

A solution of acetyl chloride (0.12 g, 1.5 mmole) in dry acetonitrile (2 ml) was added dropwise to a stirred solution of 3-carbamoyl-2-(2,4-dichlorophenyl)-1-(1H-1,2,4-triazol-1-yl)propan-2-ol (0.314 g., 1 mmole) and pyridine (0.12 g., 1.5 mmole) in dry acetonitrile (2 ml) at -20° C. The solution was allowed to warm to room temperature and was stirred at room temperature for a further 18 hours. The solvent was then removed under reduced pressure and the residue was partitioned between water (10 ml) and chloroform (40 ml). The organic phase was separated, dried over MgSO4 and evaporated. The residue was chromatographed on silica eluting with 10:1 (v:v) chloroform/methanol and the fractions containing the product were combined, evaporated, and recrystallized from diisopropyl ether to furnish the title compound, (67 mg., 19%), m.p. 148°-150° C.

Workup

  1. customThe solvent was then removed under reduced pressure
  2. customthe residue was partitioned between water (10 ml) and chloroform (40 ml)
  3. customThe organic phase was separated
  4. dry with materialdried over MgSO4
  5. customevaporated
  6. customThe residue was chromatographed on silica eluting with 10:1 (v:v) chloroform/methanol
  7. additionthe fractions containing the product
  8. customevaporated
  9. customrecrystallized from diisopropyl ether

Sources & evidence

ORD record
ord-fa5a6b848e2c43779697ce275706b117
Source dataset
uspto-grants-1985_03
Patent number
US04503063

Reaction notes

Loading…