Ethylenediamine → 4-(Aminomethyl)-N,N,N'-trimethylbenzenesulfonimidamide

HRID 527364Notes

Reaction equation

HRID 527364 reaction equation
O=C1C2C(=CC=CC=2)C(=O)[N:3]1[CH2:12][C:13]1[CH:18]=[CH:17][C:16]([S:19](=[N:24][CH3:25])([N:21]([CH3:23])[CH3:22])=[O:20])=[CH:15][CH:14]=1.C(#N)C.O1CCCC1.NCCN>C(O)C>[NH2:3][CH2:12][C:13]1[CH:14]=[CH:15][C:16]([S:19](=[N:24][CH3:25])([N:21]([CH3:22])[CH3:23])=[O:20])=[CH:17][CH:18]=1

Participants

6

Reactant 4

HCID 3301Ethylenediamine2×HCID 6342AcetonitrileHCID 8028TetrahydrofuranHCID 899787664-((1,3-Dioxoisoindolin-2-yl)methyl)-N,N,N'-trimethyl-benzene-sulfonimidamide

Product 1

HCID 899788134-(Aminomethyl)-N,N,N'-trimethylbenzenesulfonimidamide

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
60 °C

Procedure

A solution of 4-((1,3-dioxoisoindolin-2-yl)methyl)-N,N,N′-trimethyl-benzene-sulfonimidamide (preparation 60c, 280 mg, 0.78 mmol) in a 2:1:1 mixture of acetonitrile, tetrahydrofuran and ethanol (8 mL) is treated with 1,2-diaminoethane (116 μL, 1.74 mmol). The mixture is heated at 60° C. for 5 h, and another portion of 1,2-diaminoethane (26 μL, 0.39 mmol) is added. After 1.5 h all volatiles are removed under reduced pressure. The residue is treated with dichloromethane, and the mixture is filtered. The filtrate is concentrated under reduced pressure. Yield: 172 mg (97% of theory). ESI mass spectrum: [M+H]+=228; r.t. HPLC: 0.66 min (V011_S01).

Workup

  1. customAfter 1.5 h all volatiles are removed under reduced pressure
  2. additionThe residue is treated with dichloromethane
  3. filtrationthe mixture is filtered
  4. concentrationThe filtrate is concentrated under reduced pressure
  5. customr.t
  6. custom0.66 min (V011_S01)

Sources & evidence

ORD record
ord-4c06f9cf188c439aad36fe750d84c8c3
Source dataset
uspto-grants-2016_05
Patent number
US09346794B1

Reaction notes

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