p-Bromobenzenesulfonyl chloride → HCID 4349762, compound

HRID 736615Notes

Reaction equation

HRID 736615 reaction equation
[CH2:1]([O:3][CH2:4][CH2:5][NH2:6])[CH3:2].[Br:7][C:8]1[CH:13]=[CH:12][C:11]([S:14](Cl)(=[O:16])=[O:15])=[CH:10][CH:9]=1.C(N(C(C)C)C(C)C)C.C([O-])(O)=O.[Na+]>O1CCCC1>[Br:7][C:8]1[CH:13]=[CH:12][C:11]([S:14]([NH:6][CH2:5][CH2:4][O:3][CH2:1][CH3:2])(=[O:16])=[O:15])=[CH:10][CH:9]=1

Participants

6

Reactant 4

HCID 7396p-Bromobenzenesulfonyl chlorideHCID 66970EthoxyethylamineHCID 81531DiisopropylethylamineHCID 516892Sodium Bicarbonate

Product 1

HCID 4349762HCID 4349762, compoundYield 90.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

(2-Ethoxyethyl)amine (0.178 g, 2.0 mmol) was added to a stirred solution of 4-bromobenzenesulfonyl chloride (0.256 g, 1.0 mmol) in tetrahydrofuran (10 mL) at 0 C, followed by addition of N-ethyl-N,N-diisopropylamine (0.260 g, 2.0 mmol). The resulting mixture was stirred at 0° C. for 10 min, and was then allowed to return to room temperature. A saturated solution of NaHCO3 (aq) was added and the phases were separated, and the aqueous phase was extracted with ethyl acetate. The combined organic phases were dried over Na2SO4, and the solvent was evaporated to give the crude product. Purification by column chromatography using ethyl acetate/heptane (1:10 to 1:1) as the eluent gave 0.278 g (90% yield) of the title compound: MS (ES) m/z 294 and 296 (M++1).

Workup

  1. customto return to room temperature
  2. customthe phases were separated
  3. extractionthe aqueous phase was extracted with ethyl acetate
  4. dry with materialThe combined organic phases were dried over Na2SO4
  5. customthe solvent was evaporated
  6. customto give the crude product
  7. customPurification by column chromatography

Sources & evidence

ORD record
ord-db6f703cb8b841839907edb926334d73
Source dataset
uspto-grants-2009_09
Patent number
US07595319B2

Reaction notes

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