Chloromethyl Methyl Ether → HCID 67000857, compound

HRID 1434676Notes

Reaction equation

HRID 1434676 reaction equation
[H-].[Na+].[Br:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[NH:14][C:13]([CH2:15][C:16]3[CH:21]=[CH:20][CH:19]=[C:18]([Cl:22])[CH:17]=3)=[N:12][N:11]=2)=[CH:6][CH:5]=1.[CH2:23](Cl)[O:24][CH3:25]>C1COCC1.CCOC(C)=O>[Br:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[N:14]([CH2:23][O:24][CH3:25])[C:13]([CH2:15][C:16]3[CH:21]=[CH:20][CH:19]=[C:18]([Cl:22])[CH:17]=3)=[N:12][N:11]=2)=[CH:6][CH:5]=1.[Br:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[N:11]([CH2:23][O:24][CH3:25])[N:12]=[C:13]([CH2:15][C:16]3[CH:21]=[CH:20][CH:19]=[C:18]([Cl:22])[CH:17]=3)[N:14]=2)=[CH:6][CH:5]=1

Participants

7

Reactant 3

HCID 7864Chloromethyl Methyl EtherHCID 24758Sodium hydrideHCID 178478073HCID 178478073, compound

Product 2

HCID 67000857HCID 67000857, compoundYield 150%HCID 67001368HCID 67001368, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a suspension of NaH (1.1 mmol in 60% mineral oil) in THF (3 mL) at 0° C. was added 3-(4-bromo-phenyl)-5-(3-chloro-benzyl)-4H-[1,2,4]triazole (1.0 mmol). After the mixture was stirred for 30 min, MOMCl (1.0 mmol) was added and the mixture was stirred from 0° C. to room temperature overnight. The reaction mixture was diluted with EtOAc, washed with brine, dried over MgSO4, and concentrated in vacuo. The crude product was purified by column chromatography to give 3-(4-bromo-phenyl)-5-(3-chloro-benzyl)-4-methoxymethyl-4H-[1,2,4]triazole and 5-(4-bromo-phenyl)-3-(3-chloro-benzyl)-1-methoxymethyl-1H-[1,2,4]triazole (0.75 mmol) as a mixture of two isomers (4:1).

Workup

  1. stirringthe mixture was stirred from 0° C. to room temperature overnight
  2. washwashed with brine
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated in vacuo
  5. customThe crude product was purified by column chromatography

Sources & evidence

ORD record
ord-18f6220c404642439de8a52f35b9893d
Source dataset
uspto-grants-2009_11
Patent number
US07615569B2

Reaction notes

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