Diisopropyl Ether → HCID 18393044, compound

HRID 1739504Notes

Reaction equation

HRID 1739504 reaction equation
[H-].[Na+].[CH2:3]([C:5]1[S:9][C:8]([NH:10][C:11](=[O:16])[C:12]([F:15])([F:14])[F:13])=[N:7][N:6]=1)[CH3:4].[Br:17][C:18]1[CH:25]=[CH:24][C:21]([CH2:22]Br)=[CH:20][CH:19]=1.C(OC(C)C)(C)C>CN(C)C=O.CCCCCC.C(OCC)(=O)C>[CH2:3]([C:5]1[S:9][C:8](=[N:10][C:11](=[O:16])[C:12]([F:14])([F:15])[F:13])[N:7]([CH2:22][C:21]2[CH:24]=[CH:25][C:18]([Br:17])=[CH:19][CH:20]=2)[N:6]=1)[CH3:4]

Participants

8

Reactant 4

HCID 7914Diisopropyl EtherHCID 24758Sodium hydrideHCID 685274-Bromobenzyl bromideHCID 1221966HCID 1221966, compound

Product 1

HCID 18393044HCID 18393044, compoundYield 62.9%

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 8058HexaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a suspension of sodium hydride (4.4 g) in N,N-dimethylformamide (100 ml) was added 5-ethyl-2-trifluoroacetylamino-1,3,4-thiadiazole (24 g) in three portions on ice. After stirring at the same temperature for 30 minutes, to the resulting mixture was added 4-bromobenzyl bromide (25 g), followed by stirring at room temperature for one hour. To the reaction mixture, ethyl acetate (500 ml) was added. The resulting mixture was washed successively with 10% aqueous citric acid solution and water and was dried over anhydrous magnesium sulfate, followed by removal through distillation. The residue so obtained was dispersed in a 2:3 mixed solvent of diisopropyl ether and n-hexane, collected by filtration and then dried, whereby 24.8 g of the title compound was obtained.

Workup

  1. stirringby stirring at room temperature for one hour
  2. washThe resulting mixture was washed successively with 10% aqueous citric acid solution and water
  3. dry with materialwas dried over anhydrous magnesium sulfate
  4. customfollowed by removal through distillation
  5. customThe residue so obtained
  6. filtrationcollected by filtration
  7. customdried

Sources & evidence

ORD record
ord-a952160fa4ad47a9b4f4d12605d449c7
Source dataset
uspto-grants-1999_10
Patent number
US05965738

Reaction notes

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