Tert-Butylamine → N-tert-butyl-4-fluorobenzenesulfonamide

HRID 2217466Notes

Reaction equation

HRID 2217466 reaction equation
[C:1]([NH2:5])([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.[F:13][C:14]1[CH:19]=[CH:18][C:17]([S:20](Cl)(=[O:22])=[O:21])=[CH:16][CH:15]=1>C(Cl)Cl>[C:1]([NH:5][S:20]([C:17]1[CH:18]=[CH:19][C:14]([F:13])=[CH:15][CH:16]=1)(=[O:22])=[O:21])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 6385Tert-ButylamineHCID 8471TriethylamineHCID 95884-Fluorobenzenesulfonyl chloride

Product 1

HCID 669058N-tert-butyl-4-fluorobenzenesulfonamideYield 80.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Into a DCM solution (50 mL) of tert-butylamine (5.9 mL, 56.5 mmol) and triethylamine (7.16 mL, 51.3 mmol) at 0° C. was slowly added a DCM solution (20 mL) of 4-fluoro-benzenesulfonyl chloride (10 g, 51.3 mmol), and the reaction stirred at RT for 19 h. The reaction was concentrated and the resulting solid recrystalized from ether/hexanes to get the product (9.5 g, 80%)as white crystals. MS: APCI (AP+): 230.1 (M)+.

Workup

  1. concentrationThe reaction was concentrated
  2. customthe resulting solid recrystalized from ether/hexanes

Sources & evidence

ORD record
ord-a05935f707b9414a8275980c88f1a1fb
Source dataset
uspto-grants-2008_08
Patent number
US07407972B2

Reaction notes

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