Sodium Hydroxide → HCID 178527345, compound

HRID 2354899Notes

Reaction equation

HRID 2354899 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([N:11]2[CH:19]3[CH2:20][CH2:21][CH2:22][CH:12]2[C:13]2[N:14]=[N:15][N:16](S(C4C=CC(Cl)=CC=4)(=O)=O)[C:17]=2[CH2:18]3)(=[O:10])=[O:9])=[CH:4][CH:3]=1.[OH-].[Na+]>C1COCC1.O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([N:11]2[CH:19]3[CH2:20][CH2:21][CH2:22][CH:12]2[C:13]2[N:14]=[N:15][NH:16][C:17]=2[CH2:18]3)(=[O:9])=[O:10])=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 5967948912,5-Bis(4-chloro-benzenesulfonyl)-3,4,5,12-tetraaza-tricyclo[6.3.1.02,6]dodeca-2(6),3-diene

Product 1

HCID 178527345HCID 178527345, compoundYield 55.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
75 °C

Procedure

To 12,5-bis(4-chloro-benzenesulfonyl)-3,4,5,12-tetraaza-tricyclo[6.3.1.02,6]dodeca-2(6),3-diene (15 mg, 0.029 mmol) in THF (200 μL) was added H2O (100 μM) followed by 1M NaOH solution in H2O (100 μL). The mixture was heated at 75° C. for 3 hr. The mixture was partitioned between EtOAc/H2O. The organic layer was washed with brine, dried and concentrated. The residue was purified by prep TLC to 12-(4-Chloro-benzenesulfonyl)-3,4,5,12-tetraaza-tricyclo[6.3.1.02,6]dodeca-2(6),3-diene (5.3 mg, 0.016 mmol, 54% yield). MS (ES) m/e 339.0 (M+H)

Workup

  1. customThe mixture was partitioned between EtOAc/H2O
  2. washThe organic layer was washed with brine
  3. customdried
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-6e24b09f150c4fde981bc4330b8be9d9
Source dataset
uspto-grants-2010_07
Patent number
US07754712B2

Reaction notes

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