Trifluoroacetic acid → HCID 59441746, compound

HRID 1014348Notes

Reaction equation

HRID 1014348 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([N:12]2[CH2:18][CH2:17][CH2:16][NH:15][CH2:14][CH2:13]2)[CH:6]=[CH:7][C:8]=1[N+:9]([O-:11])=[O:10].C(O)(C(F)(F)F)=O.C(N(CC)CC)C.[CH3:33][S:34](Cl)(=[O:36])=[O:35]>ClCCl>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([N:12]2[CH2:18][CH2:17][CH2:16][N:15]([S:34]([CH3:33])(=[O:36])=[O:35])[CH2:14][CH2:13]2)[CH:6]=[CH:7][C:8]=1[N+:9]([O-:11])=[O:10]

Participants

6

Reactant 4

HCID 6422Trifluoroacetic acidHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 59442091HCID 59442091, compound

Product 1

HCID 59441746HCID 59441746, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

1-[3-(methyloxy)-4-nitrophenyl]hexahydro-1H-1,4-diazepine (as the TFA salt) (1.0 g, 2.08 mmol) was dissolved in dichloromethane (10 mL) and triethylamine (0.87 mL, 6.25 mmol). Methanesulfonyl chloride (0.24 mL, 3.12 mmol) was added slowly and stirred at rt for 30 min. At this time the reaction mixture was diluted with dichloromethane and washed with a saturated bicarbonate solution, water and a saturated sodium chloride solution, dried over Na2SO4 and filtered. Solvents were removed under reduced pressure to afford 1-[3-(methyloxy)-4-nitrophenyl]-4-(methylsulfonyl)hexahydro-1H-1,4-diazepine. (0.737 g, 2.24 mmol) as a yellow/brown solid. ESIMS (M+H)+=330.

Workup

  1. washwashed with a saturated bicarbonate solution, water
  2. dry with materiala saturated sodium chloride solution, dried over Na2SO4
  3. filtrationfiltered
  4. customSolvents were removed under reduced pressure

Sources & evidence

ORD record
ord-44275c52cac748dbb112f9f1665dff0e
Source dataset
uspto-grants-2011_07
Patent number
US07981903B2

Reaction notes

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