Sodium hydride → HCID 68955586, compound

HRID 1784943Notes

Reaction equation

HRID 1784943 reaction equation
[H-].[Na+].[CH3:3][N:4]([CH3:18])[NH:5][C:6]([C:8]1[CH:9]=[C:10]([CH:15]=[CH:16][CH:17]=1)[C:11]([O:13][CH3:14])=[O:12])=[O:7].[CH3:19][C:20]1[N:21]=[C:22]([CH2:25]Br)[S:23][CH:24]=1>C1COCC1>[CH3:18][N:4]([CH3:3])[N:5]([CH2:25][C:22]1[S:23][CH:24]=[C:20]([CH3:19])[N:21]=1)[C:6]([C:8]1[CH:9]=[C:10]([CH:15]=[CH:16][CH:17]=1)[C:11]([O:13][CH3:14])=[O:12])=[O:7]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 18361324HCID 18361324, compoundHCID 689609911,3-Benzenedicarboxylic acid, monomethyl ester, 2,2-dimethylhydrazide

Product 1

HCID 68955586HCID 68955586, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
3.5 °C

Procedure

To the sodium hydride (16 mg, 0.68 mmol) in THF (3 ml) at 0° C., methyl 3-(2,2-dimethylhydrazinecarbonyl)benzoate (100 mg, 0.45 nmol) was added. After 10 min, 4-methyl-2-bromo methyl thiazole (103 mg, 0.54 mmol) was added and reaction mixture was stirred at 3-4° C. overnight. Reaction mixture was quenched with MeOH and diluted with ethylacetate. Organic layer was washed with water, brine and dried. Crude residue was purified by column chromatography to yield 70% of methyl 3-(2,2-dimethyl-1-((4-methylthiazol-2-yl)methyl)hydrazinecarbonyl)benzoate.

Workup

  1. customreaction mixture
  2. customReaction mixture
  3. customwas quenched with MeOH
  4. additiondiluted with ethylacetate
  5. washOrganic layer was washed with water, brine
  6. customdried
  7. customCrude residue was purified by column chromatography

Sources & evidence

ORD record
ord-1828696cbe48471ca423380990a521a1
Source dataset
uspto-grants-2009_03
Patent number
US07504420B2

Reaction notes

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