Hydrochloric Acid → 1-(5-bromo-4-chloro-2-methoxy-benzenesulfonyl)-2,3,4,5-tetrahydro-1H-benzo[b]azepine

HRID 2382685Notes

Reaction equation

HRID 2382685 reaction equation
C(Cl)Cl.[Br:4][C:5]1[C:6]([Cl:26])=[CH:7][C:8](F)=[C:9]([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:10]=1.[CH3:27][O-:28].[Na+].Cl>CO.O>[Br:4][C:5]1[C:6]([Cl:26])=[CH:7][C:8]([O:28][CH3:27])=[C:9]([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:10]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 6344Dichloromethane2×HCID 10942334Sodium MethoxideHCID 684709361-(5-bromo-4-chloro-2-fluoro-benzenesulfonyl)-2,3,4,5-tetrahydro-1H-benzo[b]azepine

Product 1

HCID 684691311-(5-bromo-4-chloro-2-methoxy-benzenesulfonyl)-2,3,4,5-tetrahydro-1H-benzo[b]azepine

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a solution of DCM (8 mL) containing 1-(5-bromo-4-chloro-2-fluoro-benzenesulfonyl)-2,3,4,5-tetrahydro-1H-benzo[b]azepine (2.35 g, 5.6 mmol) was added 25% sodium methoxide in methanol (7.5 mL). The resulting suspension was stirred at rt for 3 hrs, followed by repartitioning with DCM (45 mL) and water (50 mL). A 6 N HCl solution was added dropwise until the aqueous layer pH was 7. The organic layer was separated, washed with water (2×30 mL), dried over MgSO4, and evaporated to afford 1-(5-bromo-4-chloro-2-methoxy-benzenesulfonyl)-2,3,4,5-tetrahydro-1H-benzo[b]azepine as the pale yellow foam (2.38 g). MS: 430.0 (M+H)+; tR=6.21 min (method 4). NMR (CDCl3), δ, 8.070 (1H, s), 7.130-7.219 (3H, m), 7.025-7.082 (1H, m), 6.761 (1H, d, J=7.5 Hz), 3.868 (3H, s), 3.733 (2H, m), 2.808-2.845 (2H, m), 1.902-1.940 (2H, m), 1.568-1.667 (2H, m).

Workup

  1. customThe organic layer was separated
  2. washwashed with water (2×30 mL)
  3. dry with materialdried over MgSO4
  4. customevaporated

Sources & evidence

ORD record
ord-5604eaaf75d84c299ba1f295ed054327
Source dataset
uspto-grants-2012_09
Patent number
US08263588B2

Reaction notes

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