Hydrochloric Acid → 4-(3-chloropropoxy)-N-(2,2-dimethyl-propyl)benzenesulfonamide

HRID 1662985Notes

Reaction equation

HRID 1662985 reaction equation
[Cl:1][CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([S:12](Cl)(=[O:14])=[O:13])=[CH:8][CH:7]=1.[CH2:16]([NH2:21])[C:17]([CH3:20])([CH3:19])[CH3:18].C(N(CC)CC)C.Cl>C(Cl)Cl>[Cl:1][CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([S:12]([NH:21][CH2:16][C:17]([CH3:20])([CH3:19])[CH3:18])(=[O:14])=[O:13])=[CH:8][CH:7]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 79882NeopentylamineHCID 218847304-(3-Chloropropoxy)benzenesulfonyl chloride

Product 1

HCID 218848214-(3-chloropropoxy)-N-(2,2-dimethyl-propyl)benzenesulfonamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 3.5 g (13 mmol) of 4-(3-chloropropoxy)-benzenesulfonyl chloride in 100 ml of CH2Cl2, a solution of 1.62 g (18.56 mmol) of neopentyl amine in 15 ml of CH2Cl2 and 2.59 ml (18.56 mmol) of triethyl amine are added dropwise at 0-5° C. After stirring for 2.5 h at r.t., the reaction mixture is neutralized with 1N aqueous HCl and extracted with AcOEt. The combined extracts are washed with brine, dried over MgSO4 and concentrated under reduced pressure to give 4-(3-chloropropoxy)-N-(2,2-dimethyl-propyl)benzenesulfonamide; NMR (CDCl3): 0.879 (s, 9H), 2.20-2.35 (m, 2H), 2.66 (d, 2H, J=6.88 Hz), 3.76 (t, 2H, J=6.28 Hz), 4.20 (t, 2H, J=5.84 Hz), 4.35-4.465 (m, 1H), 6.98 (d, 2H, J=8.88 Hz), 7.77 (d, 2H, J=8.88 Hz).

Workup

  1. extractionextracted with AcOEt
  2. washThe combined extracts are washed with brine
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-eee9c214e58443f3a6b1aff732a43981
Source dataset
uspto-grants-2011_10
Patent number
US08034810B2

Reaction notes

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