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

HRID 2382681Notes

Reaction equation

HRID 2382681 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(C(C)C)CC)(C)C.O>C(Cl)Cl>[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 4

HCID 962WaterHCID 7323Benzenesulfonyl chloride, 4-chloro-3-nitro-HCID 81531DiisopropylethylamineHCID 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 90.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To 4-chloro-3-nitrobenzenesulfonyl chloride (1.0 g, 3.9 mmol) in dry DCM (10 mL), was added 2,3,4,5-tetrahydro-1H-benzo[b]azepine (0.57 g, 3.9 mmol). Diisopropylethylamine (1.3 mL, 7.8 mmol) was added and the mixture was stirred at ambient temperature for 16 hrs. DCM (20 mL) and 30 mL of water were added. The DCM layer was separated, washed with brine (20 mL×2), dried over MgSO4 and evaporated to give 1-(3-nitro-4-chloro-benzenesulfonyl)-2,3,4,5-tetrahydro-1H-benzo[b]azepine 4-1 as a yellow solid (1.3 g, 85% yield). MS: 367 (M+H)+; tR=2.98 min (method 1).

Workup

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

Sources & evidence

ORD record
ord-c9dc0309cabc49b2a9896a8f847a3bdb
Source dataset
uspto-grants-2012_09
Patent number
US08263588B2

Reaction notes

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