Sodium hydride → HCID 68642095, compound

HRID 1498948Notes

Reaction equation

HRID 1498948 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[CH:4][C:3]=1[C:9]1[S:10][C:11]([C:15]([O:20][CH3:21])([O:18][CH3:19])[CH2:16][OH:17])=[C:12]([CH3:14])[N:13]=1.[CH3:22][O:23][C:24]1[CH:31]=[CH:30][C:27]([CH2:28]Cl)=[CH:26][CH:25]=1.[H-].[Na+]>CN(C)C=O>[CH3:21][O:20][C:15]([C:11]1[S:10][C:9]([C:3]2[CH:4]=[CH:5][C:6]([CH3:8])=[CH:7][C:2]=2[CH3:1])=[N:13][C:12]=1[CH3:14])([O:18][CH3:19])[CH2:16][O:17][CH2:28][C:27]1[CH:30]=[CH:31][C:24]([O:23][CH3:22])=[CH:25][CH:26]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 699934-Methyloxybenzyl chlorideHCID 68642113HCID 68642113, compound

Product 1

HCID 68642095HCID 68642095, compoundYield 64.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To N,N-dimethylformamide (2 ml), 2-[2-(2,4-dimethylphenyl)-4-methylthiazol-5-yl]-2,2-dimethoxyethanol (100 mg) prepared in the Step 31-1-2 and 4-methoxybenzyl chloride (61 mg) were added, and 60% sodium hydride suspension in oil (20 mg) was added thereto under an argon atmosphere. Then, the mixture was stirred at a room temperature for 4 hours. Ice water was added to the reaction solution, and then the mixture was subjected to extraction with ethyl acetate. The extract was dried over anhydrous sodium sulfate, and then concentrated under a reduced pressure. The residue was purified by thin-layer chromatography (hexane:ethyl acetate=3:1) to give the title compound (90 mg, 64%).

Workup

  1. additionwere added
  2. extractionthe mixture was subjected to extraction with ethyl acetate
  3. dry with materialThe extract was dried over anhydrous sodium sulfate
  4. concentrationconcentrated under a reduced pressure
  5. customThe residue was purified by thin-layer chromatography (hexane:ethyl acetate=3:1)

Sources & evidence

ORD record
ord-67eab2ab8c65418092181b1f499b25c7
Source dataset
uspto-grants-2015_12
Patent number
US09200008B2

Reaction notes

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