Methane → HCID 58066686, compound

HRID 390412Notes

Reaction equation

HRID 390412 reaction equation
[CH3:1][O:2][C:3](=[O:19])[C:4]1[CH:9]=[CH:8][C:7]([N+:10]([O-])=O)=[CH:6][C:5]=1[CH2:13][S:14][C:15]([CH3:18])([CH3:17])[CH3:16].[CH3:20]N(C)N.C>CO>[CH2:1]([O:2][C:3](=[O:19])[C:4]1[CH:9]=[CH:8][C:7]([NH2:10])=[CH:6][C:5]=1[CH2:13][S:14][C:15]([CH3:18])([CH3:17])[CH3:16])[CH3:20]

Participants

5

Reactant 3

HCID 297MethaneHCID 59761,1-DimethylhydrazineHCID 58372755HCID 58372755, compound

Product 1

HCID 58066686HCID 58066686, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
70 °C

Procedure

2-tert-Butylsulfanylmethyl-4-nitro-benzoic acid methyl ester (5.68 g, 19.1 mmol), 1,1-dimethylhydrazine (11.6 mL, 192 mmol), and DARCO (2.0 g, 19.1 mmol) were combined in MeOH (200 mL). Ferric chloride (0.50 g, 3.1 mmol) was added, and the reaction was stirred at 70° C. for 3.5 hours. The mixture was stored in the freezer overnight, and then worked-up and purified by silica gel chromatography to give the title compound.

Workup

  1. customwas stored in the freezer overnight
  2. custompurified by silica gel chromatography

Sources & evidence

ORD record
ord-f4d35b4e3eda47d0a168e976adf39091
Source dataset
uspto-grants-2013_02
Patent number
US08383654B2

Reaction notes

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