Water → HCID 21446689, compound
Reaction equation
[C:1]([C:5]1[CH:10]=[C:9]([NH:11][S:12]([C:15]2[CH:20]=[CH:19][C:18]([CH3:21])=[CH:17][CH:16]=2)(=[O:14])=[O:13])[CH:8]=[C:7]([C:22]([CH3:25])([CH3:24])[CH3:23])[C:6]=1[OH:26])([CH3:4])([CH3:3])[CH3:2].[CH3:27][O-].[Na+].CI.O>CO>[C:1]([C:5]1[CH:10]=[C:9]([N:11]([CH3:27])[S:12]([C:15]2[CH:16]=[CH:17][C:18]([CH3:21])=[CH:19][CH:20]=2)(=[O:14])=[O:13])[CH:8]=[C:7]([C:22]([CH3:25])([CH3:24])[CH3:23])[C:6]=1[OH:26])([CH3:4])([CH3:3])[CH3:2]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 100 °C
Procedure
To a solution of 3.75 grams (0.01 mole) of the product of Example 1, 2,6-di-tert-butyl-4(p-toluenesulfonamido)phenol, and 0.54 grams (0.01 mole) of sodium methylate in 50 ml of methanol was added 1.42 grams (0.01 mole) of methyl iodide. The reaction mixture was heated with stirring for 72 hours in a pressure tube at 100° C. The reaction mixture was then cooled, poured into 150 ml of water and extracted with heptane. The heptane layer was separated and allowed to stand after cooling. Crystals formed which were isolated by filtration, washed and dried to weigh 0.5 gram and melted at 123°-142° C. Recrystallization from heptane gave 0.2 gram of crystals melting at 130°-142° C. Proton NMR spectra confirmed the expected, desired structure. (Compound 6)
Workup
- temperatureThe reaction mixture was heated
- temperatureThe reaction mixture was then cooled
- extractionextracted with heptane
- customThe heptane layer was separated
- temperatureafter cooling
- customCrystals formed which
- customwere isolated by filtration
- washwashed
- customdried
- customRecrystallization from heptane
Sources & evidence
- ORD record
- ord-023acadf260241f68d1b9e84cd2eb237
- Source dataset
- uspto-grants-1977_03
- Patent number
- US04013621
Reaction notes
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