Sodium hydride → t-Butyl N-[5-(3,5-di-t-butyl-4-hydroxyphenylthio)-2-nitrophenyl]-N-methylcarbamate

HRID 2303852Notes

Reaction equation

HRID 2303852 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([SH:16])[CH:8]=[C:9]([C:12]([CH3:15])([CH3:14])[CH3:13])[C:10]=1[OH:11])([CH3:4])([CH3:3])[CH3:2].Cl[C:18]1[CH:19]=[CH:20][C:21]([N+:33]([O-:35])=[O:34])=[C:22]([N:24]([CH3:32])[C:25](=[O:31])[O:26][C:27]([CH3:30])([CH3:29])[CH3:28])[CH:23]=1.[H-].[Na+]>CN(C)C=O>[C:1]([C:5]1[CH:6]=[C:7]([S:16][C:18]2[CH:19]=[CH:20][C:21]([N+:33]([O-:35])=[O:34])=[C:22]([N:24]([CH3:32])[C:25](=[O:31])[O:26][C:27]([CH3:28])([CH3:29])[CH3:30])[CH:23]=2)[CH:8]=[C:9]([C:12]([CH3:15])([CH3:14])[CH3:13])[C:10]=1[OH:11])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 703702,6-Di-tert-butyl-4-mercaptophenolHCID 15544598tert-butyl N-(5-chloro-2-nitrophenyl)-N-methylcarbamate

Product 1

HCID 18184967t-Butyl N-[5-(3,5-di-t-butyl-4-hydroxyphenylthio)-2-nitrophenyl]-N-methylcarbamateYield 38%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

By using 476 mg of 3,5-di-t-butyl-4-hydroxybenzenethiol, 573 mg of t-butyl N-(5-chloro-2-nitrophenyl)-N-methylcarbamate, 175 mg of sodium hydride (55% by weight) and 10 ml of anhydrous N,N-dimethylformamide, reaction and purification were carried out in a similar manner to that described in Reference Example 6, whereby 371 mg of the title compound were obtained.

Sources & evidence

ORD record
ord-5b55bb756c4b4212ac63461e7fe71f38
Source dataset
uspto-grants-2002_08
Patent number
US06432993B1

Reaction notes

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