Sodium Hydroxide → HCID 21878474, compound

HRID 723960Notes

Reaction equation

HRID 723960 reaction equation
[N:1]1[CH:5]=[C:4]([CH2:6][CH2:7][NH:8][C:9]2[S:10][C:11]3[CH:17]=[C:16]([N+:18]([O-])=O)[CH:15]=[CH:14][C:12]=3[N:13]=2)[NH:3][CH:2]=1.O.O.[Sn](Cl)Cl.[OH-].[Na+].N.CO>C(O)C.C1COCC1.C(OCC)(=O)C.C(Cl)Cl>[N:1]1[CH:5]=[C:4]([CH2:6][CH2:7][NH:8][C:9]2[S:10][C:11]3[CH:17]=[C:16]([NH2:18])[CH:15]=[CH:14][C:12]=3[N:13]=2)[NH:3][CH:2]=1

Participants

9

Reactant 4

HCID 14798Sodium HydroxideHCID 61436Stannous chloride dihydrateHCID 21705897Ammonia methanolHCID 21878470HCID 21878470, compound

Product 1

HCID 21878474HCID 21878474, compoundYield 56.5%

Reagents, catalysts & solvents 4

HCID 702EthanolSolventHCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of [2-(3H-Imidazol-4-yl)-ethyl]-(6-nitro-benzothiazol-2-yl)-amine (Example 23(b), 80 mg, 0.28 mmol) in ethanol (5 mL) and THF (1.5 mL) was added tin(II) chloride dihydrate (312 mg, 5 eq.). The mixture was heated at reflux for 2 hours. The reaction mixture was cooled to room temperature, diluted with ethyl acetate (50 mL) then treated with 2 M aqueous NaOH (20 mL). The organic layer was separated, dried over MgSO4 and concentrated to give a yellow residue. The residue was subjected to silica gel column chromatography (10–15% 2M ammonia/methanol in CH2Cl2) to give the final product (41 mg, 56%). 1H NMR (CD3OD) δ: 7.65 (s, 1H), 7.23 (d, 1H, 8.5 Hz), 6.98 (d, 1H, J=1.8 Hz), 6.91 (s, 1H), 6.72 (dd, 1H, J=1.8, 8.5 Hz), 3.64 (t, 2H, J=7.3 Hz), 2.95 (t, 2H, J=7.3 Hz).

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 2 hours
  3. customThe organic layer was separated
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated
  6. customto give a yellow residue

Sources & evidence

ORD record
ord-b2a441d8247a403b982e2cc629faeeff
Source dataset
uspto-grants-2006_11
Patent number
US07141595B2

Reaction notes

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