Water → HCID 68286080, compound

HRID 1053309Notes

Reaction equation

HRID 1053309 reaction equation
[C:1]([NH2:5])([CH3:4])([CH3:3])[CH3:2].[Br:6][C:7]1[C:16]2[CH2:15][CH2:14][CH2:13][CH2:12][C:11]=2[C:10]([S:17](Cl)(=[O:19])=[O:18])=[CH:9][CH:8]=1.O>O1CCCC1>[Br:6][C:7]1[C:16]2[CH2:15][CH2:14][CH2:13][CH2:12][C:11]=2[C:10]([S:17]([NH:5][C:1]([CH3:4])([CH3:3])[CH3:2])(=[O:19])=[O:18])=[CH:9][CH:8]=1

Participants

5

Reactant 3

HCID 962WaterHCID 6385Tert-ButylamineHCID 86705034HCID 86705034, compound

Product 1

HCID 68286080HCID 68286080, compoundYield 17.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
25 °C

Procedure

Tert-butyl amine [8.5 g, 12.32 ml, 116.0 mmol) was added dropwise to a stirred suspension of 4-bromo-5,6,7,8-tetrahydronaphthalene-1-sulfonyl chloride (59a, 12.0 g, 38.8 mmol) in 150 ml tetrahydrofuran at 0° C. The reaction mixture was then stirred at a temperature of about 25° C. for 2 hours. The progress of the reaction was monitored by TLC. Water (100 ml) was added to the reaction mixture, and the mixture so obtained was extracted with ethyl acetate (2×150 ml). The combined organic layer was then dried over sodium sulphate, and the dried organic layer was concentrated under reduced pressure to obtain a crude product, which was then purified by column chromatography over silica gel (100-200 mesh) using 15% ethyl acetate in hexanes as an eluent to obtain the title compound (2.34 g, 17.4%).

Workup

  1. customthe mixture so obtained
  2. extractionwas extracted with ethyl acetate (2×150 ml)
  3. dry with materialThe combined organic layer was then dried over sodium sulphate
  4. concentrationthe dried organic layer was concentrated under reduced pressure
  5. customto obtain a crude product, which
  6. customwas then purified by column chromatography over silica gel (100-200 mesh)

Sources & evidence

ORD record
ord-f557b00cf8594acf9253ccec5e3f9667
Source dataset
uspto-grants-2016_07
Patent number
US09393247B2

Reaction notes

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