2-Propanethiol → 1-Nitro-3-[(propan-2-ylsulfanyl)methyl]benzene
Reaction equation
C[O-].[Na+].[CH3:4][CH:5]([SH:7])[CH3:6].[N+:8]([C:11]1[CH:12]=[C:13]([CH:16]=[CH:17][CH:18]=1)[CH2:14]Cl)([O-:10])=[O:9]>CO>[N+:8]([C:11]1[CH:18]=[CH:17][CH:16]=[C:13]([CH2:14][S:7][CH:5]([CH3:6])[CH3:4])[CH:12]=1)([O-:10])=[O:9]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -15 °C
Procedure
A solution of sodium methoxide (15.5 mL, 25 wt % in methanol) was diluted with methanol (85 mL) and treated with 2-propanethiol (6.3 mL) at room temperature for 60 minutes, cooled to −15° C., treated with 3-nitrobenzylchloride (10 g) in 3 portions, kept for 2 hours at −15° C., then the temperature was increased to room temperature. The reaction mixture was concentrated in vacuo, treated with diethyl ether (300 mL), washed with water (2×100 mL) and brine (100 mL), dried with sodium sulfate and evaporated to dryness. The title compound (12.3 g) was thus obtained and used without further purification.
Workup
- temperaturethe temperature was increased to room temperature
- concentrationThe reaction mixture was concentrated in vacuo
- additiontreated with diethyl ether (300 mL)
- washwashed with water (2×100 mL) and brine (100 mL)
- dry with materialdried with sodium sulfate
- customevaporated to dryness
Sources & evidence
- ORD record
- ord-e82b50983e4647c39c463c09cc7b179c
- Source dataset
- uspto-grants-2015_08
- Patent number
- US09108926B2
Reaction notes
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