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 2196070Notes

Reaction equation

HRID 2196070 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-2cdcd2609f934ee983f2331ea58e2221
Source dataset
uspto-grants-2012_12
Patent number
US08338406B2

Reaction notes

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