Ethylenediamine → HCID 86710160, compound

HRID 705385Notes

Reaction equation

HRID 705385 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:9][C:10]3[CH:18]=[C:17]([N:19]([CH2:24][C:25]4[CH:30]=[CH:29][C:28]([O:31][CH3:32])=[CH:27][CH:26]=4)[S:20]([CH3:23])(=[O:22])=[O:21])[C:16]([O:33][CH:34]([CH3:36])[CH3:35])=[CH:15][C:11]=3[C:12]=2[CH:13]=O)=[CH:4][CH:3]=1.[CH2:37]([NH2:40])[CH2:38][NH2:39].BrN1C(=O)CCC1=O>ClCCl>[NH:39]1[CH2:38][CH2:37][N:40]=[C:13]1[C:12]1[C:11]2[CH:15]=[C:16]([O:33][CH:34]([CH3:36])[CH3:35])[C:17]([N:19]([CH2:24][C:25]3[CH:30]=[CH:29][C:28]([O:31][CH3:32])=[CH:27][CH:26]=3)[S:20]([CH3:23])(=[O:22])=[O:21])=[CH:18][C:10]=2[O:9][C:8]=1[C:5]1[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=1

Participants

5

Reactant 3

HCID 3301EthylenediamineHCID 67184N-bromobutanimideHCID 86710158HCID 86710158, compound

Product 1

HCID 86710160HCID 86710160, compoundYield 77.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

N-(2-(4-fluorophenyl)-3-formyl-5-isopropoxybenzofuran-6-yl)-N-(4-methoxybenzyl)methanesulfonamide (0.65 g, 1.27 mmol) was dissolved in dichloromethane, and powdered 4 A molecular sieves (0.7 g) were added. The slurry was cooled to 0° C. in an ice bath and treated with dropwise addition of ethylenediamine (0.1 mL, 1.4 mmol). The resulting slurry was stirred under nitrogen for 30 minutes, then solid N-bromosuccinimide was added in one portion and the reaction was stirred at room temperature overnight. The reaction mixture was diluted with 100 mL dichloromethane and filtered through diatomaceous earth. The organic filtrate was washed with 10% aqueous sodium bicarbonate, 10% aqueous sodium chloride, dried over anhydrous sodium sulfate(s), filtered and the solvent was removed in vacuo leaving a foamy solid (0.54 g, 77%) which was placed under vacuum for 24 hours. The title compound was used without purification.

Workup

  1. additionwere added
  2. stirringthe reaction was stirred at room temperature overnight
  3. filtrationfiltered through diatomaceous earth
  4. washThe organic filtrate was washed with 10% aqueous sodium bicarbonate, 10% aqueous sodium chloride
  5. dry with materialdried over anhydrous sodium sulfate(s)
  6. filtrationfiltered
  7. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-0b55b88280534f0ba2abbf49c0f2bad3
Source dataset
uspto-grants-2015_11
Patent number
US09173887B2

Reaction notes

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