2-Propanethiol → 1-Nitro-3-[(propan-2-ylsulfanyl)methyl]benzene
Reaction equation
[Na].[CH3:2][CH:3]([SH:5])[CH3:4].[N+:6]([C:9]1[CH:10]=[C:11]([CH:14]=[CH:15][CH:16]=1)[CH2:12]Cl)([O-:8])=[O:7]>CO>[N+:6]([C:9]1[CH:16]=[CH:15][CH:14]=[C:11]([CH2:12][S:5][CH:3]([CH3:4])[CH3:2])[CH:10]=1)([O-:8])=[O:7]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -15 °C
Procedure
A solution of sodium methoxyde (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-83ff9f2f25b74a57b4cd7db9c70d60b8
- Source dataset
- uspto-grants-2014_12
- Patent number
- US08916557B2
Reaction notes
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