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

HRID 2382697Notes

Reaction equation

HRID 2382697 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-feff5a707e0e49a883ca62e0a686d9ce
Source dataset
uspto-grants-2012_09
Patent number
US08263588B2

Reaction notes

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