3-Methoxypropylamine → N-(3-Methoxy-propyl)-C-(3-nitro-phenyl)-methanesulfonamide

HRID 1890981Notes

Reaction equation

HRID 1890981 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][CH2:5][NH2:6].C(N(CC)CC)C.[N+:14]([C:17]1[CH:18]=[C:19]([CH2:23][S:24](Cl)(=[O:26])=[O:25])[CH:20]=[CH:21][CH:22]=1)([O-:16])=[O:15]>C(#N)C.O>[CH3:1][O:2][CH2:3][CH2:4][CH2:5][NH:6][S:24]([CH2:23][C:19]1[CH:20]=[CH:21][CH:22]=[C:17]([N+:14]([O-:16])=[O:15])[CH:18]=1)(=[O:25])=[O:26]

Participants

6

Reactant 3

HCID 16723-MethoxypropylamineHCID 8471TriethylamineHCID 13196775(3-Nitrophenyl)methanesulfonyl chloride

Product 1

HCID 59411197N-(3-Methoxy-propyl)-C-(3-nitro-phenyl)-methanesulfonamide

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

3-metoxypropylamine (0.184 mL, 1.80 mmol) and triethylamine (0.3 mL) were added to a solution of (3-Nitrophenyl)methanesulfonyl chloride (0.35 g, 1.50 mmol) in acetonitrile (10 mL). The resulting solution was vigorously stirred for 3 h at room temperature and then diluted with cold water (30 ml), which lead to the formation of a precipitate. The precipitate was filtered off, washed with water (2×10 mL) and dried. Yield of N-(3-methoxy-propyl)-C-(3-nitro-phenyl)-methanesulfonamide 0.31 g (72%).

Workup

  1. filtrationThe precipitate was filtered off
  2. washwashed with water (2×10 mL)
  3. customdried

Sources & evidence

ORD record
ord-5bbdea83689e4b53a397a72becb014f8
Source dataset
uspto-grants-2013_08
Patent number
US08507498B2

Reaction notes

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