Benzenesulfonyl chloride, 4-chloro-3-nitro- → 1-(3-nitro-4-chloro-benzenesulfonyl)-2,3,4,5-tetrahydro-1H-benzo[b]azepine

HRID 1891374Notes

Reaction equation

HRID 1891374 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8](Cl)(=[O:10])=[O:9])=[CH:4][C:3]=1[N+:12]([O-:14])=[O:13].[NH:15]1[CH2:21][CH2:20][CH2:19][CH2:18][C:17]2[CH:22]=[CH:23][CH:24]=[CH:25][C:16]1=2.C(N(CC)CC)C>C(Cl)Cl.O>[N+:12]([C:3]1[CH:4]=[C:5]([S:8]([N:15]2[CH2:21][CH2:20][CH2:19][CH2:18][C:17]3[CH:22]=[CH:23][CH:24]=[CH:25][C:16]2=3)(=[O:10])=[O:9])[CH:6]=[CH:7][C:2]=1[Cl:1])([O-:14])=[O:13]

Participants

6

Reactant 3

HCID 7323Benzenesulfonyl chloride, 4-chloro-3-nitro-HCID 8471TriethylamineHCID 5765032,3,4,5-tetrahydro-1H-1-benzazepine

Product 1

HCID 231200581-(3-nitro-4-chloro-benzenesulfonyl)-2,3,4,5-tetrahydro-1H-benzo[b]azepineYield 98.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

To 4-chloro-3-nitrobenzenesulfonyl chloride (2.56 g, 10 mmol) in dry DCM (20 mL) was added 2,3,4,5-tetrahydro-1H-benzo[b]azepine (1.54 g, 10.5 mmol) and triethylamine (3.3 mL, 25 mmol). The mixture was stirred at ambient temperature for 16 hrs. The mixture was then diluted with 40 mL of DCM and 30 mL of water. The organic layer was separated, washed with brine (2×20 mL), dried over MgSO4, and evaporated to afford 1-(3-nitro-4-chloro-benzenesulfonyl)-2,3,4,5-tetrahydro-1H-benzo[b]azepine as a yellow solid (3.6 g).

Workup

  1. customThe organic layer was separated
  2. washwashed with brine (2×20 mL)
  3. dry with materialdried over MgSO4
  4. customevaporated

Sources & evidence

ORD record
ord-94896664d1694f0fa87fdbbba22d201e
Source dataset
uspto-grants-2013_08
Patent number
US08507536B2

Reaction notes

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