Ethyl Acetate → 2-Chloro-5-(2,3,4,5-tetrahydro-benzo[b]azepine-1-sulfonyl)-phenylamine

HRID 1891375Notes

Reaction equation

HRID 1891375 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([S:11]([N:14]2[CH2:20][CH2:19][CH2:18][CH2:17][C:16]3[CH:21]=[CH:22][CH:23]=[CH:24][C:15]2=3)(=[O:13])=[O:12])[CH:7]=[CH:8][C:9]=1[Cl:10])([O-])=O.S(S([O-])=O)([O-])=O.[Na+].[Na+].C(OCC)(=O)C.[NH4+].[Cl-]>C1COCC1.O>[Cl:10][C:9]1[CH:8]=[CH:7][C:6]([S:11]([N:14]2[CH2:20][CH2:19][CH2:18][CH2:17][C:16]3[CH:21]=[CH:22][CH:23]=[CH:24][C:15]2=3)(=[O:12])=[O:13])=[CH:5][C:4]=1[NH2:1]

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 24489Sodium DithioniteHCID 25517Ammonium ChlorideHCID 231200581-(3-nitro-4-chloro-benzenesulfonyl)-2,3,4,5-tetrahydro-1H-benzo[b]azepine

Product 1

HCID 231203012-Chloro-5-(2,3,4,5-tetrahydro-benzo[b]azepine-1-sulfonyl)-phenylamineYield 100.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To 1-(3-nitro-4-chloro-benzenesulfonyl)-2,3,4,5-tetrahydro-1H-benzo[b]azepine (3.6 g, 10 mmol) in THF (50 mL) and water (50 mL) was added sodium hydrosulfite (10.2 g, 50 mmol). The mixture was stirred at ambient temperature for 2 hrs. Ethyl acetate (150 mL) and sat. NH4Cl (150 mL) were added. The organic layer was separated, washed with brine (2×50 mL) and dried over MgSO4. Concentration and purification by silica gel column chromatography eluting with hexane/ethyl acetate (4/1 to 1/1) yielded 2-chloro-5-(2,3,4,5-tetrahydro-benzo[b]azepine-1-sulfonyl)-phenylamine as pale yellow solid (3.4 g). MS: 337.0 (M+H)+; tR=2.85 min (method 1).

Workup

  1. customThe organic layer was separated
  2. washwashed with brine (2×50 mL)
  3. dry with materialdried over MgSO4
  4. concentrationConcentration and purification by silica gel column chromatography
  5. washeluting with hexane/ethyl acetate (4/1 to 1/1)

Sources & evidence

ORD record
ord-2a7a88f1fb1841c7b9ef2bea963637d8
Source dataset
uspto-grants-2013_08
Patent number
US08507536B2

Reaction notes

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