Water → HCID 28754020, compound

HRID 1484924Notes

Reaction equation

HRID 1484924 reaction equation
[Br:1][C:2]1[S:6][C:5]([S:7](Cl)(=[O:9])=[O:8])=[CH:4][CH:3]=1.[CH2:11]([NH2:14])[CH2:12][NH2:13].O>C(Cl)Cl>[NH2:13][CH2:12][CH2:11][NH:14][S:7]([C:5]1[S:6][C:2]([Br:1])=[CH:3][CH:4]=1)(=[O:9])=[O:8]

Participants

5

Reactant 3

HCID 962WaterHCID 3301EthylenediamineHCID 27339245-Bromothiophene-2-sulfonyl chloride

Product 1

HCID 28754020HCID 28754020, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

A mixture of 5-bromothiophene-2-sulfonyl chloride (2.5 g, 9.6 mmol, 1.0 eq) in CH2Cl2 (100 mL) was stirred at 0° C., ethane-1, 2-diamine (2.3 g, 38.24 mmol, 4 eq) was added drop-wise. Then, the mixture was stirred at 0° C. for 0.5 h. Water was added and extracted with EA (6×80 ml). The combined organic layers were dried (Na2SO4), filtered and concentrated to give N-(2-aminoethyl)-5-bromothiophene-2-sulfonamide (2.51 g, 92.0%). LC-MS (m/z)=284.1 [M+H]+.

Workup

  1. stirringThen, the mixture was stirred at 0° C. for 0.5 h
  2. extractionextracted with EA (6×80 ml)
  3. dry with materialThe combined organic layers were dried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-61b990f164f9406aad45e214f107028e
Source dataset
uspto-grants-2016_08
Patent number
US09422271B2

Reaction notes

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