Ethylenediamine → HCID 3105263, compound

HRID 1350379Notes

Reaction equation

HRID 1350379 reaction equation
[CH2:1]([NH2:4])[CH2:2][NH2:3].C(N([CH2:10][CH3:11])CC)C.[CH3:12][O:13][C:14]1[CH:19]=[CH:18][C:17]([S:20](Cl)(=[O:22])=[O:21])=[CH:16][CH:15]=1>C(Cl)Cl>[CH3:12][O:13][C:14]1[CH:19]=[CH:18][C:17]([S:20]([NH:3][CH2:2][CH2:1][NH:4][S:20]([C:11]2[CH:10]=[CH:19][C:14]([O:13][CH3:12])=[CH:15][CH:16]=2)(=[O:22])=[O:21])(=[O:22])=[O:21])=[CH:16][CH:15]=1

Participants

5

Reactant 3

HCID 3301EthylenediamineHCID 74014-Methoxybenzenesulfonyl chlorideHCID 8471Triethylamine

Product 1

HCID 3105263HCID 3105263, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Combine ethylenediamine (0.9 g, 15 mmol) in CH2Cl2 (50 mL) and mix with triethylamine (3.03 g, 30 mmol). Cool the mixture on a ice-water bath and add dropwise 4-methoxybenzenesulfonyl chloride (6.2 g, 30 mmol) in CH2Cl2 (50 mL). Warm the reaction to room temperature and stir overnight. Wash the reaction with 1N HCl (100 mL), sat. NaHCO3, brine, dry over Na2SO4, and concentrate the crude product in vacuo. Purification by flash chromatography (CH2Cl2/EtOAc=5:1) gives the title compound: Mass spectrum (electrospray): (m/z)=401.1 (M+1); 1H NMR (CDCl3): δ7.77–7.74 (m, 4H), 6.99–6.96 (m, 4H), 4.95 (br, 2H), 3.87 (s, 6H), 3.06–3.04 (m, 4H).

Workup

  1. temperatureCool the mixture on a ice-water bath
  2. temperatureWarm
  3. customthe reaction to room temperature
  4. washWash
  5. customthe reaction with 1N HCl (100 mL), sat. NaHCO3, brine
  6. dry with materialdry over Na2SO4
  7. concentrationconcentrate the crude product in vacuo
  8. customPurification by flash chromatography (CH2Cl2/EtOAc=5:1)

Sources & evidence

ORD record
ord-bd144b8339df45b28477c79c7fc38481
Source dataset
uspto-grants-2007_05
Patent number
US07214673B2

Reaction notes

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