Ethylenediamine → HCID 9994532, compound

HRID 354059Notes

Reaction equation

HRID 354059 reaction equation
[C:1]([CH2:3][C:4]1[C:9]2[CH:10]=[CH:11][O:12][C:8]=2[C:7]([NH:13][S:14]([CH3:17])(=[O:16])=[O:15])=[CH:6][CH:5]=1)#[N:2].[CH2:18](N)[CH2:19][NH2:20]>C(=S)=S>[NH:2]1[CH2:18][CH2:19][N:20]=[C:1]1[CH2:3][C:4]1[C:9]2[CH:10]=[CH:11][O:12][C:8]=2[C:7]([NH:13][S:14]([CH3:17])(=[O:15])=[O:16])=[CH:6][CH:5]=1

Participants

4

Reactant 2

HCID 3301EthylenediamineHCID 23512987HCID 23512987, compound

Product 1

HCID 9994532HCID 9994532, compoundYield 93.7%

Reagents, catalysts & solvents 1

HCID 6348Carbon DisulfideCatalyst

Procedure

A mixture of N-(4-cyanomethyl-benzofuran-7-yl)-methanesulfonamide (1.0 g, 4.0 mmole), ethylene diamine (8 mL, 119.7 mmoles), and carbon disulfide (one drop) was microwaved at 140° C. for 30 minutes in a Smith creator™. The reaction mixture was transferred into a large beaker (1 L) and the reaction vessel was rinsed with methanol (5 mL). Ether (600 mL) was added to the reaction mixture and insoluble material settled at the bottom of the container. The ether solution was removed by decantation. The residue was purified by flash column chromatography over silica gel eluting with 8% methanol in dichloromethane with 0.1% concentrated ammonium hydroxide to give N-[4-(4,5-dihydro-1H-imidazol-2-ylmethyl)-benzofuran-7-yl]-methanesulfonamide as a solid (1.1 g, 85%).

Workup

  1. customwas microwaved at 140° C. for 30 minutes in a Smith creator™
  2. washthe reaction vessel was rinsed with methanol (5 mL)
  3. additionEther (600 mL) was added to the reaction mixture and insoluble material
  4. customThe ether solution was removed by decantation
  5. customThe residue was purified by flash column chromatography over silica gel eluting with 8% methanol in dichloromethane with 0.1% concentrated ammonium hydroxide

Sources & evidence

ORD record
ord-6943d8382e03434b8fcd347e5bb62d12
Source dataset
uspto-grants-2004_06
Patent number
US06756395B2

Reaction notes

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