Sodium hydride → 2,2,3,3-Tetramethylcyclopropanecarboxylic acid [6-fluoro-3-(2-methoxyethyl)-3H-benzothiazol-2-ylidene]-amide

HRID 78411Notes

Reaction equation

HRID 78411 reaction equation
[F:1][C:2]1[CH:20]=[CH:19][C:5]2[N:6]=[C:7]([NH:9][C:10]([CH:12]3[C:14]([CH3:16])([CH3:15])[C:13]3([CH3:18])[CH3:17])=[O:11])[S:8][C:4]=2[CH:3]=1.[H-].[Na+].[CH3:23][O:24][CH2:25][CH2:26]Br>CN(C=O)C.C1COCC1>[F:1][C:2]1[CH:20]=[CH:19][C:5]2[N:6]([CH2:26][CH2:25][O:24][CH3:23])[C:7](=[N:9][C:10]([CH:12]3[C:13]([CH3:18])([CH3:17])[C:14]3([CH3:16])[CH3:15])=[O:11])[S:8][C:4]=2[CH:3]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 809722-Bromoethyl methyl etherHCID 86618903N-(6-fluoro-1,3-benzothiazol-2-yl)-2,2,3,3-tetramethylcyclopropanecarboxamide

Product 1

HCID 686230162,2,3,3-Tetramethylcyclopropanecarboxylic acid [6-fluoro-3-(2-methoxyethyl)-3H-benzothiazol-2-ylidene]-amide

Reagents, catalysts & solvents 1

HCID 21974620tetrahydrofuran N,N-dimethylformamideSolvent

Procedure

To a solution of the product of Example 112A (1 equiv) in 1:1 DMF/THF (0.1 M) was added sodium hydride (60% dispersion in mineral oil, 1.2 equiv) and 2-bromoethyl methyl ether (1.2 equiv).

Sources & evidence

ORD record
ord-b0f6e5c438ab400daaa69330c3215cf9
Source dataset
uspto-grants-2014_09
Patent number
US08841334B2

Reaction notes

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