Ethylamine → HCID 67335526, compound

HRID 1043668Notes

Reaction equation

HRID 1043668 reaction equation
Br[C:2]1[S:6][C:5]2=[N:7][CH:8]=[C:9]([S:10](Cl)(=[O:12])=[O:11])[N:4]2[N:3]=1.C([N:16]([CH2:19][CH3:20])CC)C.[CH2:21]([NH2:23])[CH3:22]>C(#N)C>[CH2:21]([NH:23][S:10]([C:9]1[N:4]2[C:5]([S:6][C:2]([NH:16][CH2:19][CH3:20])=[N:3]2)=[N:7][CH:8]=1)(=[O:12])=[O:11])[CH3:22]

Participants

5

Reactant 3

HCID 6341EthylamineHCID 8471TriethylamineHCID 47003642HCID 47003642, compound

Product 1

HCID 67335526HCID 67335526, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
0 °C

Procedure

2-Bromo-imidazo[2,1-b][1,3,4]thiadiazole-5-sulfonyl chloride (0.15 g; 0.50 mmol) was dissolved in dry acetonitrile (5 mL). Triethylamine (69 μL; 0.50 mmol) was added, and the reaction mixture was cooled at 0° C. for 10 minutes before adding ethylamine (2M in tetrahydrofuran, 2.5 mL; 5.0 mmol). The reaction was allowed to reach room temperature and stirred overnight. The solvent was evaporated and the crude taken up in dichloromethane and sodium hydrogen carbonate solution. Extraction with dichloromethane, drying over sodium sulphate and evaporation of the solvent gave a brown gum that was purified on silica gel (ethyl acetate:hexane 4:1). The title product 2-ethylamino-imidazo[2,1-b][1,3,4]thiadiazole-5-sulfonic acid ethylamide was isolated as a white powder (43 mg, 31%).

Workup

  1. customto reach room temperature
  2. customThe solvent was evaporated
  3. extractionExtraction with dichloromethane
  4. dry with materialdrying over sodium sulphate and evaporation of the solvent
  5. customgave a brown gum that
  6. customwas purified on silica gel (ethyl acetate:hexane 4:1)

Sources & evidence

ORD record
ord-f179cac0692043e5b821c89e55ca6bd8
Source dataset
uspto-grants-2013_10
Patent number
US08563550B2

Reaction notes

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