Triethylamine → HCID 22500778, compound
Reaction equation
[Cl:1][C:2]1[S:6][C:5]([S:7](Cl)(=[O:9])=[O:8])=[CH:4][CH:3]=1.[CH2:11]([CH:13]([CH2:18][CH2:19][OH:20])[CH:14](C)[CH2:15][OH:16])[CH3:12].C([N:23](CC)CC)C.CCOC(C)=O.CCCCCC>C(Cl)Cl>[Cl:1][C:2]1[S:6][C:5]([S:7]([NH:23][CH:14]([CH2:15][OH:16])[CH:13]([CH2:11][CH3:12])[CH2:18][CH2:19][OH:20])(=[O:9])=[O:8])=[CH:4][CH:3]=1Participants
Conditions
- Temperature
- 25 °C
Procedure
5-Chlorothiophene-2-sulfonyl chloride (6.4 g, 24.48 mmol) was added dropwise (5 min) as a solution in CH2Cl2 (5 mL) to a 0° C. solution of 3-ethyl-2-methylpentane-1,5-diol (2.85 g, 19.34 mmol) in CH2Cl2 (30 mL) and triethylamine (5.66 mL, 40.81 mmol). The solution was allowed to warm to 25° C. overnight (19 h). An aliquot was taken and TLC (1:1 EtOAc-hexane) indicated that reaction was complete. It was diluted with CH2Cl2 (50 mL) and the organic layer was washed with 1N HCl (2×50 mL) and saturated aqueous NaCl (50 mL). The organic layer was dried over MgSO4, filtered and concentrated to obtain a crude oil (4.9 g). The crude product was purified by column chromatography, silica gel 230-400 mesh, eluant: 1:4 EtOAc-hexane to afford 5-chloro-N-[2-ethyl-4-hydroxy-1-(hydroxymethyl)butyl]thiophene-2-sulfonamide as an amorphous white solid (0.450 g, 7.3%). Mass Spectrum (−ESI): 326 (M−H)−.
Workup
- washthe organic layer was washed with 1N HCl (2×50 mL) and saturated aqueous NaCl (50 mL)
- dry with materialThe organic layer was dried over MgSO4
- filtrationfiltered
- concentrationconcentrated
- customto obtain a crude oil (4.9 g)
- customThe crude product was purified by column chromatography, silica gel 230-400 mesh, eluant
Sources & evidence
- ORD record
- ord-366a6857807548599c05528d05931af4
- Source dataset
- uspto-grants-2010_11
- Patent number
- US07842718B2
Reaction notes
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