alpha-Chloro-m-nitrotoluene → HCID 70976446, compound
Reaction equation
[Na].[CH:2]1([SH:7])[CH2:6][CH2:5][CH2:4][CH2:3]1.[N+:8]([C:11]1[CH:12]=[C:13]([CH:16]=[CH:17][CH:18]=1)[CH2:14]Cl)([O-:10])=[O:9]>CO>[CH:2]1([S:7][CH2:14][C:13]2[CH:16]=[CH:17][CH:18]=[C:11]([N+:8]([O-:10])=[O:9])[CH:12]=2)[CH2:6][CH2:5][CH2:4][CH2:3]1Participants
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 cyclopentanethiol (7.3 mL) at room temperature for 60 minutes, cooled to −15° C., treated with 3-nitrobenzylchloride (10.0 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 (350 mL), washed with water (2×150 mL) and brine (100 mL), dried with sodium sulfate and evaporated to dryness. The title compound (14.9 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 (350 mL)
- washwashed with water (2×150 mL) and brine (100 mL)
- dry with materialdried with sodium sulfate
- customevaporated to dryness
Sources & evidence
- ORD record
- ord-e01feabb354143a79fee48393b2320e4
- Source dataset
- uspto-grants-2014_12
- Patent number
- US08916557B2
Reaction notes
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