Triethylamine → N-[2-Chloro-4-(tetrahydro-pyran-2-yloxy)-benzyl]-N-(4-iodo-phenyl)-2,4,6-trimethyl-benzenesulfonamide

HRID 1827570Notes

Reaction equation

HRID 1827570 reaction equation
[Cl:1][C:2]1[CH:16]=[C:15]([O:17][CH:18]2[CH2:23][CH2:22][CH2:21][CH2:20][O:19]2)[CH:14]=[CH:13][C:3]=1[CH2:4][NH:5][C:6]1[CH:11]=[CH:10][C:9]([I:12])=[CH:8][CH:7]=1.C(N(CC)CC)C.[C:31]1([CH3:43])[CH:36]=[C:35]([CH3:37])[CH:34]=[C:33]([CH3:38])[C:32]=1[S:39](Cl)(=[O:41])=[O:40].C(=O)(O)[O-].[Na+]>C(Cl)Cl.CN(C1C=CN=CC=1)C>[Cl:1][C:2]1[CH:16]=[C:15]([O:17][CH:18]2[CH2:23][CH2:22][CH2:21][CH2:20][O:19]2)[CH:14]=[CH:13][C:3]=1[CH2:4][N:5]([C:6]1[CH:7]=[CH:8][C:9]([I:12])=[CH:10][CH:11]=1)[S:39]([C:32]1[C:33]([CH3:38])=[CH:34][C:35]([CH3:37])=[CH:36][C:31]=1[CH3:43])(=[O:41])=[O:40]

Participants

7

Reactant 4

HCID 8471Triethylamine4×HCID 130462-Mesitylenesulfonyl chloride3×HCID 516892Sodium BicarbonateHCID 22137418[2-Chloro-4-(tetrahydro-pyran-2-yloxy)-benzyl]-(4-iodophenyl)-amine

Product 1

HCID 22137336N-[2-Chloro-4-(tetrahydro-pyran-2-yloxy)-benzyl]-N-(4-iodo-phenyl)-2,4,6-trimethyl-benzenesulfonamideYield 54.4%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalyst2×HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of [2-chloro-4-(tetrahydro-pyran-2-yloxy)-benzyl]-(4-iodophenyl)-amine (3.00 g, 6.76 mmol) in 4 mL methylene chloride was added triethylamine (2.84 mL, 20.3 mmol) and 2-mesitylenesulfonyl chloride (2.96 g, 13.5 mmol). The reaction mixture was stirred at room temperature overnight. Additional triethylamine (1 mL, 7.15 mmol) was added and the reaction mixture was allowed to stir at room temperature overnight. DMAP was added and the reaction mixture was allowed to stir at room temperature for three days. Additional methylene chloride (2 mL), triethylamine (1 mL, 7.15 mmol) and 2-mesitylenesulfonyl chloride (1.00 g, 4.57 mmol) were added. The reaction mixture was stirred at 30° C. overnight. Additional triethylamine (2.84 mL, 20.3 mmol) and DMAP were added and the reaction was stirred at 30° C. overnight. Additional 2-mesitylenesulfonyl chloride (0.54 g, 2.47 mmol) was added and the reaction mixture was stirred at 30° C. overnight. Saturated aqueous sodium bicarbonate was added and the mixture was extracted with methylene chloride. The organic layer was dried (magnesium sulfate) and concentrated. Medium pressure silica gel chromatography of the residue afforded 2.30 g (54%) of the title compound of Step B.

Workup

  1. stirringto stir at room temperature overnight
  2. stirringto stir at room temperature for three days
  3. stirringThe reaction mixture was stirred at 30° C. overnight
  4. stirringthe reaction was stirred at 30° C. overnight
  5. stirringthe reaction mixture was stirred at 30° C. overnight
  6. extractionthe mixture was extracted with methylene chloride
  7. dry with materialThe organic layer was dried (magnesium sulfate)
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-47c5e4e6f21a4b85b8aea145ab2ddce6
Source dataset
uspto-grants-2006_05
Patent number
US07053212B2

Reaction notes

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