Water → HCID 66637332, compound

HRID 1094637Notes

Reaction equation

HRID 1094637 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:9]([NH:11][S:12]([C:14]([CH3:17])([CH3:16])[CH3:15])=[O:13])[CH3:10])[CH:5]=[CH:6][C:7]=1[NH2:8].C1N=CN([C:23](N2C=NC=C2)=[O:24])C=1.O>C1COCC1.C(Cl)Cl>[CH3:17][C:14]([S:12]([NH:11][CH:9]([C:4]1[CH:5]=[CH:6][C:7]2[NH:8][C:23](=[O:24])[NH:1][C:2]=2[CH:3]=1)[CH3:10])=[O:13])([CH3:16])[CH3:15]

Participants

5

Reactant 3

HCID 962WaterHCID 682631,1'-CarbonyldiimidazoleHCID 66637050HCID 66637050, compound

Product 1

HCID 66637332HCID 66637332, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 21919333Tetrahydrofurane dichloromethaneSolvent

Procedure

A mixture of N-[1-(3,4-diaminophenyl)ethyl]-2-methylpropane-2-sulfinamide and CDI (569 mg, 3.51 mmol) in THF-DCM (10 ml-10 ml) was refluxed for 6 hours. After cooling to the room temperture, water (10 mL) was added to the mixture. The mixture was extracted with EtOAc (150 ml) and organic layer was washed with brine (30 ml), dried over sodium sulfate and concentrated. The residue was recrystallized from EtOAc to afford 430 mg (65%) of the title compound as a pale brown solid. 1H NMR (300 MHz, DMSO-d6) δ ppm 1.11 (9H, s), 1.38 (3H, d, J=7.3 Hz), 4.37-4.28 (1H, m), 5.53 (1H, d, J=6.6 Hz), 6.84 (1H, d, J=7.3 Hz), 6.93 (1H, d, J=8.1 Hz), 6.99 (1H, s), 10.54 (1H, br.s), 10.60 (1H, br.s). MS (ESI) m/z 282 (M+H)+, 280 (M−H)−.

Workup

  1. temperaturewas refluxed for 6 hours
  2. additionwas added to the mixture
  3. extractionThe mixture was extracted with EtOAc (150 ml) and organic layer
  4. washwas washed with brine (30 ml)
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated
  7. customThe residue was recrystallized from EtOAc

Sources & evidence

ORD record
ord-1456908fa4c441c7b3bb17738d4d0a93
Source dataset
uspto-grants-2012_03
Patent number
US08134004B2

Reaction notes

Loading…