Water → methyl N-(3-phenylbenzyl)N-(2-propynyl)carbamate

HRID 1168030Notes

Reaction equation

HRID 1168030 reaction equation
[C:1]1([C:7]2[CH:8]=[C:9]([CH:16]=[CH:17][CH:18]=2)[CH2:10][NH:11][C:12](=[O:15])[O:13][CH3:14])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Na+].[CH2:21](Br)[C:22]#[CH:23].O>O1CCCC1>[C:1]1([C:7]2[CH:8]=[C:9]([CH:16]=[CH:17][CH:18]=2)[CH2:10][N:11]([CH2:23][C:22]#[CH:21])[C:12](=[O:15])[O:13][CH3:14])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7842Propargyl bromideHCID 24758Sodium hydrideHCID 12090300methyl N-(3-phenylbenzyl)carbamate

Product 1

HCID 12090305methyl N-(3-phenylbenzyl)N-(2-propynyl)carbamateYield 66.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

0.70 g of methyl N-(3-phenylbenzyl)carbamate in tetrahydrofuran (20 ml) was stirred together with 0.15 g of 60% sodium hydride at room temperature for 30 minutes. 0.52 g of propargyl bromide was added dropwise at room temperature, and the resulting solution was stirred overnight. After the reaction, the reaction solution was poured into water and extracted with ethyl acetate, and the organic layer was separated, dried over anhydrous magnesium sulfate and evaporated under reduced pressure for removal of the solvent. The residue was purified by silica gel column chromatography to give 0.54 g of methyl N-(3-phenylbenzyl)N-(2-propynyl)carbamate as a yellow transparent viscous liquid.

Workup

  1. customAfter the reaction
  2. extractionextracted with ethyl acetate
  3. customthe organic layer was separated
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customevaporated under reduced pressure for removal of the solvent
  6. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-2cc273e41362477eac54574d2e47ddc6
Source dataset
uspto-grants-2003_09
Patent number
US06620961B1

Reaction notes

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