Ethylenediamine → HCID 9994532, compound

HRID 2217374Notes

Reaction equation

HRID 2217374 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 creators. 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 chromratography 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 creators
  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 chromratography over silica gel eluting with 8% methanol in dichloromethane with 0.1% concentrated ammonium hydroxide

Sources & evidence

ORD record
ord-fa764b7db15a419e810ed8700b5a52fb
Source dataset
uspto-grants-2008_08
Patent number
US07407980B2

Reaction notes

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