Tert-Butylhydroquinone → HCID 18461476, compound

HRID 2303872Notes

Reaction equation

HRID 2303872 reaction equation
[C:1]([C:5]1[CH:11]=[C:10]([OH:12])[CH:9]=[CH:8][C:6]=1[OH:7])([CH3:4])([CH3:3])[CH3:2].Cl[C:14]1[CH:15]=[CH:16][C:17]([N+:29]([O-:31])=[O:30])=[C:18]([N:20]([CH3:28])[C:21](=[O:27])[O:22][C:23]([CH3:26])([CH3:25])[CH3:24])[CH:19]=1.[H-].[Na+]>CN(C)C=O>[C:1]([C:5]1[CH:11]=[C:10]([CH:9]=[CH:8][C:6]=1[OH:7])[O:12][C:14]1[CH:15]=[CH:16][C:17]([N+:29]([O-:31])=[O:30])=[C:18]([N:20]([CH3:28])[C:21](=[O:27])[O:22][C:23]([CH3:24])([CH3:25])[CH3:26])[CH:19]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 16043Tert-ButylhydroquinoneHCID 24758Sodium hydrideHCID 15544598tert-butyl N-(5-chloro-2-nitrophenyl)-N-methylcarbamate

Product 1

HCID 18461476HCID 18461476, compoundYield 32.5%

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-butylhydroquinone (1.66 g), t-butyl N-(5-chloro-2-nitrophenyl)-N-methylcarbamate (2.87 g), sodium hydride (55 wt. %, 0.87 g) and anhydrous N,N-dimethylformamide (20 ml) and the reaction mixture was purified by chromatography on a silica gel column using n-hexane/ethyl acetate=4/1 to give t-butyl N-[5-(3-t-butyl-4-hydroxyphenoxy)-2-nitrophenyl]-N-methylcarbamate (1.35 g), of which Rf value was 0.45 in thin layer chromatography on a silica gel plate using n-hexane/ethyl acetate=3/1 and t-butyl N-[5-(2-t-butyl-4-hydroxyphenoxy)-2-nitrophenyl]-N-methylcarbamate (1.11 g), of which Rf value was 0.35 in thin layer chromatography on a silica gel plate using n-hexane/ethyl acetate=3/1.

Workup

  1. customthe reaction mixture was purified by chromatography on a silica gel column

Sources & evidence

ORD record
ord-8242d8f63f7549248bcf07849f258aac
Source dataset
uspto-grants-2002_08
Patent number
US06432993B1

Reaction notes

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