Water → HCID 66927322, compound

HRID 1484925Notes

Reaction equation

HRID 1484925 reaction equation
[NH2:1][CH2:2][CH2:3][NH:4][S:5]([C:8]1[S:9][C:10]([Br:13])=[CH:11][CH:12]=1)(=[O:7])=[O:6].CCN(C(C)C)C(C)C.[C:23](Cl)(=[O:28])[C:24]([CH3:27])([CH3:26])[CH3:25].O>C(Cl)Cl>[Br:13][C:10]1[S:9][C:8]([S:5]([NH:4][CH2:3][CH2:2][NH:1][C:23](=[O:28])[C:24]([CH3:27])([CH3:26])[CH3:25])(=[O:6])=[O:7])=[CH:12][CH:11]=1

Participants

6

Reactant 4

HCID 962WaterHCID 62493Pivaloyl chlorideHCID 81531DiisopropylethylamineHCID 28754020HCID 28754020, compound

Product 1

HCID 66927322HCID 66927322, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

A mixture of N-(2-aminoethyl)-5-bromothiophene-2-sulfonamide (2.5 g, 8.77 mmol, 1.0 eq) and DIPEA (3.4 g, 26.3 mmol, 3.0 eq) in CH2Cl2 (100 mL) was stirred at 0° C., pivaloyl chloride (2.1 g, 17.5 mmol, 2 equiv.) was added drop-wise. Then, the mixture was stirred at 0° C. for 0.5 h. Water was added and the reaction was extracted with EA (3×80 ml). The combined organic layers were dried (Na2SO4), filtered, evaporated and purified by silica gel chromatography (PE/EA=10:1 as eluant) to afford N-(2-(5-bromothiophene-2-sulfonamido)ethyl)pivalamide (3.07 g, 95.0%). LC-MS (m/z)=368.9 [M+H]+.

Workup

  1. stirringThen, the mixture was stirred at 0° C. for 0.5 h
  2. extractionthe reaction was extracted with EA (3×80 ml)
  3. dry with materialThe combined organic layers were dried (Na2SO4)
  4. filtrationfiltered
  5. customevaporated
  6. custompurified by silica gel chromatography (PE/EA=10:1 as eluant)

Sources & evidence

ORD record
ord-47c222279396438aaf60d74a3fd4b102
Source dataset
uspto-grants-2016_08
Patent number
US09422271B2

Reaction notes

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