N-methyl-2-pyrrolidone → HCID 71226959, compound

HRID 704958Notes

Reaction equation

HRID 704958 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([O:8][C:9]2[CH:14]=[CH:13][C:12]([Cl:15])=[CH:11][CH:10]=2)[CH:5]=[CH:4][C:3]=1[C:16]1([CH2:19][CH3:20])[CH2:18][O:17]1.[OH-].[Na+].N1C=[CH:26][N:25]=[N:24]1.[Cl-].[NH4+].[CH3:30][N:31]1CCCC1=O>>[Cl:1][C:2]1[CH:7]=[C:6]([O:8][C:9]2[CH:14]=[CH:13][C:12]([Cl:15])=[CH:11][CH:10]=2)[CH:5]=[CH:4][C:3]=1[C:16]([OH:17])([CH2:19][CH3:20])[CH2:18][N:25]1[CH:26]=[N:31][CH:30]=[N:24]1

Participants

6

Reactant 5

HCID 13387N-methyl-2-pyrrolidoneHCID 14798Sodium HydroxideHCID 25517Ammonium ChlorideHCID 86717735HCID 86717735, compoundHCID 178418936HCID 178418936, compound

Product 1

HCID 71226959HCID 71226959, compound

Conditions

Temperature
140 °C

Procedure

To 2-[2-chloro-4-(4-chlorophenoxy)phenyl]-2-ethyl-oxirane (216.0 g, 0.63 mol) dissolved in N-methyl-2-pyrrolidon (2 L) was added sodium hydroxide (62.87 g, 1.57 mol) and triazole (217.1 g, 3.14 mol) at room temperature. The mixture was then stirred for 12 hours at 140° C. A solution of ammonium chloride and ice water was then added, the mixture extracted with MTBE and washed with an aqueous solution of lithium chloride. The crude residue was purified by recrystallization in diisopropylether to give 2-[2-chloro-4-(4-chlorophenoxy)phenyl]-1-(1,2,4-triazol-1-yl)butan-2-ol compound as a colorless solid (127.0 g, 51%; m.p.=140-142° C.).

Workup

  1. extractionthe mixture extracted with MTBE
  2. washwashed with an aqueous solution of lithium chloride
  3. customThe crude residue was purified by recrystallization in diisopropylether

Sources & evidence

ORD record
ord-d141f4d160b54c5593da59aedd2a5554
Source dataset
uspto-grants-2015_11
Patent number
US09173402B2

Reaction notes

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