Water → HCID 86661624, compound

HRID 1843687Notes

Reaction equation

HRID 1843687 reaction equation
[H-].[Na+].[CH3:3][O:4][C:5]1[CH:12]=[CH:11][C:8]([CH2:9][OH:10])=[CH:7][CH:6]=1.Cl[C:14]1[CH:15]=[CH:16][C:17]([N+:29]([O-:31])=[O:30])=[C:18]([CH2:20][NH:21][C:22](=[O:28])[O:23][C:24]([CH3:27])([CH3:26])[CH3:25])[CH:19]=1.O>CN(C=O)C>[CH3:3][O:4][C:5]1[CH:12]=[CH:11][C:8]([CH2:9][O:10][C:14]2[CH:15]=[CH:16][C:17]([N+:29]([O-:31])=[O:30])=[C:18]([CH2:20][NH:21][C:22](=[O:28])[O:23][C:24]([CH3:27])([CH3:25])[CH3:26])[CH:19]=2)=[CH:7][CH:6]=1

Participants

6

Reactant 4

HCID 962WaterHCID 77384-Methoxybenzyl alcoholHCID 24758Sodium hydrideHCID 71357443tert-Butyl [(5-chloro-2-nitrophenyl)methyl]carbamate

Product 1

HCID 86661624HCID 86661624, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

Sodium hydride (63%, 25 g, 656 mmol) was added to a solution of 4-methoxybenzyl alcohol (90.3 g, 654 mmol) and tert-butyl (5-chloro-2-nitrophenyl)methylcarbamate (US200216506 A1, 156 g, 544 mmol) in DMF (1.4 L) at room temperature, and the mixture was stirred at 80° C. for four hours. After leaving to cool, water (1.5 L) was added to the reaction mixture. The precipitated solid was collected by filtration to obtain the title compound (209 g, 99%) as a yellow solid.

Workup

  1. customAfter leaving
  2. temperatureto cool
  3. filtrationThe precipitated solid was collected by filtration

Sources & evidence

ORD record
ord-93ffd683b57d413183d662e8d9ca45fe
Source dataset
uspto-grants-2015_02
Patent number
US08946264B2

Reaction notes

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