p-Chlorothiophenol → 2-[(4-Chlorophenyl)thio]ethanamine
Reaction equation
[Na].Br.Br[CH2:4][CH2:5][NH2:6].[Cl:7][C:8]1[CH:13]=[CH:12][C:11]([SH:14])=[CH:10][CH:9]=1>C(O)C>[Cl:7][C:8]1[CH:13]=[CH:12][C:11]([S:14][CH2:4][CH2:5][NH2:6])=[CH:10][CH:9]=1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 75 °C
Procedure
A solution of sodium metal (22.5 mg, 0.98 mmol) in ethanol (2.0 mL) was treated with 2-bromoethylamine hydrobromide (100.0 mg, 0.49 mmol) and 4-chlorobenzenethiol (71.0 mg, 0.49 mmol), heated to 75° C. for 18 hours, and concentrated. The concentrate was partitioned between water (2.0 mL) and diethyl ether (5.0 mL) and the organic phase was dried (MgSO4), filtered, and concentrated to provide the desired product. MS (DCI) m/e 188 (M+H)+.
Workup
- concentrationconcentrated
- customThe concentrate was partitioned between water (2.0 mL) and diethyl ether (5.0 mL)
- dry with materialthe organic phase was dried (MgSO4)
- filtrationfiltered
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-6ef45e2a20434ab6894e17d65ea660fb
- Source dataset
- uspto-grants-2009_03
- Patent number
- US07504512B2
Reaction notes
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