Triethylamine → N-(3-(1-ethyl-3,3,5-trimethyl-2,4-dioxo-2,3,4,5-tetrahydro-1H-benzo[b][1,4]diazepin-7-yloxy)propyl)-2-nitrobenzenesulfonamide

HRID 1183087Notes

Reaction equation

HRID 1183087 reaction equation
C(N(CC)CC)C.[NH2:8][CH2:9][CH2:10][CH2:11][O:12][C:13]1[CH:30]=[CH:29][C:16]2[N:17]([CH2:27][CH3:28])[C:18](=[O:26])[C:19]([CH3:25])([CH3:24])[C:20](=[O:23])[N:21]([CH3:22])[C:15]=2[CH:14]=1.[N+:31]([C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][C:35]=1[S:40](Cl)(=[O:42])=[O:41])([O-:33])=[O:32]>ClCCl.O>[CH2:27]([N:17]1[C:18](=[O:26])[C:19]([CH3:24])([CH3:25])[C:20](=[O:23])[N:21]([CH3:22])[C:15]2[CH:14]=[C:13]([O:12][CH2:11][CH2:10][CH2:9][NH:8][S:40]([C:35]3[CH:36]=[CH:37][CH:38]=[CH:39][C:34]=3[N+:31]([O-:33])=[O:32])(=[O:41])=[O:42])[CH:30]=[CH:29][C:16]1=2)[CH3:28]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 155402-Nitrobenzenesulfonyl chlorideHCID 686735217-(3-Aminopropoxy)-1-ethyl-3,3,5-trimethyl-1,5-dihydrobenzo[b][1,4]diazepine-2,4-dione

Product 1

HCID 68672787N-(3-(1-ethyl-3,3,5-trimethyl-2,4-dioxo-2,3,4,5-tetrahydro-1H-benzo[b][1,4]diazepin-7-yloxy)propyl)-2-nitrobenzenesulfonamideYield 97%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

Triethylamine (0.8 ml, 5.7 mmol) was added to a dichloromethane solution (50 ml) of 7-(3-aminopropoxy)-1-ethyl-3,3,5-trimethyl-1,5-dihydrobenzo[b][1,4]diazepine-2,4-dione (1.22 g, 3.8 mmol) and ice-cooled. o-Nitrobenzenesulfonyl chloride (1.03 g, 4.2 mmol) was added to the resulting mixture, and stirred at room temperature for 2 hours. Water was added to the reaction mixture, and extraction with dichloromethane was performed. The organic layer was washed with water and a saturated sodium chloride aqueous solution, in this order, then dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=1:1→0:1). The purified product was concentrated to dryness under reduced pressure to thereby obtain 1.86 g (yield: 97%) of N-(3-(1-ethyl-3,3,5-trimethyl-2,4-dioxo-2,3,4,5-tetrahydro-1H-benzo[b][1,4]diazepin-7-yloxy)propyl)-2-nitrobenzenesulfonamide as a white amorphous solid.

Workup

  1. temperaturecooled
  2. washThe organic layer was washed with water
  3. dry with materiala saturated sodium chloride aqueous solution, in this order, then dried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=1:1→0:1)
  6. concentrationThe purified product was concentrated to dryness under reduced pressure

Sources & evidence

ORD record
ord-9a4d5ccd369a4967b2a0d4b57a5ef5f0
Source dataset
uspto-grants-2014_03
Patent number
US08664217B2

Reaction notes

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