Sodium hydride → HCID 18537685, compound

HRID 2303917Notes

Reaction equation

HRID 2303917 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9](=[O:15])[O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[CH:4][CH:3]=1.Cl[C:17]1[CH:18]=[CH:19][C:20]([N+:32]([O-:34])=[O:33])=[C:21]([N:23]([CH3:31])[C:24](=[O:30])[O:25][C:26]([CH3:29])([CH3:28])[CH3:27])[CH:22]=1.[H-].[Na+]>CN(C)C=O>[C:11]([O:10][C:9]([NH:8][C:5]1[CH:4]=[CH:3][C:2]([O:1][C:17]2[CH:18]=[CH:19][C:20]([N+:32]([O-:34])=[O:33])=[C:21]([N:23]([CH3:31])[C:24](=[O:30])[O:25][C:26]([CH3:27])([CH3:28])[CH3:29])[CH:22]=2)=[CH:7][CH:6]=1)=[O:15])([CH3:12])([CH3:14])[CH3:13]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 2756771N-Boc-4-hydroxyanilineHCID 15544598tert-butyl N-(5-chloro-2-nitrophenyl)-N-methylcarbamate

Product 1

HCID 18537685HCID 18537685, compoundYield 82.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In a similar manner to that described in Reference Example 6, a reaction was carried out using t-butyl (4-hydroxyphenyl)carbamate (15.6 g), t-butyl N-(5-chloro-2-nitrophenyl)-N-methylcarbamate (21 g), sodium hydride (55 wt. %, 3.22 g) and anhydrous N,N-dimethylformamide (130 ml) and the reaction mixture was purified to give the title compound (27.7 g).

Workup

  1. customthe reaction mixture was purified

Sources & evidence

ORD record
ord-f86c15d5224043fe979af3001431bd9c
Source dataset
uspto-grants-2002_08
Patent number
US06432993B1

Reaction notes

Loading…