N-methyl-2-pyrrolidone → HCID 71225831, compound

HRID 2280115Notes

Reaction equation

HRID 2280115 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([O:8][C:9]2[CH:14]=[CH:13][C:12]([F:15])=[CH:11][C:10]=2[F:16])[CH:5]=[CH:4][C:3]=1[C:17]1([CH3:20])[CH2:19][O:18]1.N1C=[CH:24][N:23]=[N:22]1.[OH-].[Na+].[CH3:28][N:29]1C(=O)CCC1>CC(OC)(C)C>[Cl:1][C:2]1[CH:7]=[C:6]([O:8][C:9]2[CH:14]=[CH:13][C:12]([F:15])=[CH:11][C:10]=2[F:16])[CH:5]=[CH:4][C:3]=1[C:17]([OH:18])([CH3:20])[CH2:19][N:23]1[CH:24]=[N:29][CH:28]=[N:22]1

Participants

6

Reactant 4

HCID 13387N-methyl-2-pyrrolidoneHCID 14798Sodium HydroxideHCID 86719001HCID 86719001, compoundHCID 178418936HCID 178418936, compound

Product 1

HCID 71225831HCID 71225831, compound

Reagents, catalysts & solvents 1

HCID 15413tert-Butyl methyl etherSolvent

Conditions

Temperature
120 °C

Procedure

2-[2-chloro-4-(2,4-difluorophenoxy)phenyl]-2-methyl-oxirane (5.0 g), triazole (5.24 g) and NaOH (1.52 g) were dissolved in NMP (50 mL) and the reaction mixture heated to 120° C. and stirred for 15 h. The reaction mixture was diluted with MTBE (200 mL) and extracted three times with 100 mL H2O. The organic phase was washed with sat. aq. NaCl-sol and dried over Na2SO4. After evaporation and column chromatography (CH2Cl2/MeOH, O-20% MeOH), 2-[2-chloro-4-(2,4-difluorophenoxy)phenyl]-1-(1,2,4-triazol-1-yl)propan-2-ol (2.7 g) was obtained as an orange oil.

Workup

  1. extractionextracted three times with 100 mL H2O
  2. washThe organic phase was washed with sat. aq. NaCl-sol
  3. dry with materialdried over Na2SO4
  4. customAfter evaporation and column chromatography (CH2Cl2/MeOH

Sources & evidence

ORD record
ord-5d287d8ecf984b0cb5d8a19fe9452d12
Source dataset
uspto-grants-2015_09
Patent number
US09137996B2

Reaction notes

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