4-Toluenesulfonyl chloride → HCID 15870294, compound

HRID 2257260Notes

Reaction equation

HRID 2257260 reaction equation
[C:1]1([CH3:11])[CH:6]=[CH:5][C:4]([S:7](Cl)(=[O:9])=[O:8])=[CH:3][CH:2]=1.Cl.Cl.[CH2:14]([NH:16][CH:17]([CH3:21])[CH2:18][CH2:19][NH2:20])[CH3:15]>C(Cl)Cl.[OH-].[Na+]>[C:1]1([CH3:11])[CH:6]=[CH:5][C:4]([S:7]([N:16]([CH2:14][CH3:15])[CH:17]([CH3:21])[CH2:18][CH2:19][NH:20][S:7]([C:4]2[CH:5]=[CH:6][C:1]([CH3:11])=[CH:2][CH:3]=2)(=[O:9])=[O:8])(=[O:9])=[O:8])=[CH:3][CH:2]=1

Participants

5

Reactant 2

HCID 73974-Toluenesulfonyl chlorideHCID 86585021HCID 86585021, compound

Product 1

HCID 15870294HCID 15870294, compoundYield 39.4%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 14798Sodium HydroxideSolvent

Conditions

Temperature
0 °C

Procedure

A solution of p-toluenesulfonyl chloride (17.01 g, 89.2 mmol) in CH2Cl2 (300 mL) was added to a solution of II (8.89 g, 47.0 mmol) in 1N NaOH (300 mL) which had been cooled to 0° C. After addition was complete, the biphasic mixture was stirred for 14 hours (0° C. to room temperature). The layers were separated and the aqueous portion was extracted with CH2Cl2 (2×50 mL). The combined organic phase was washed with 1N HCl (2×100 mL) and H2O (100 mL) and evaporated in vacuo. Column chromatography on silica gel eluting with 3% EtOH/CHCl3 produced 7.46 g (39%) of III. NMR δ0.77 (d, 3 H, J=7), 1.15 (t, 3 H, J=7), 1.45-1.76 (m, 2H), 2.40 (s, 6H), 2.79-3.25 (m, 4H), 3.70-4.08 (m, 1H), 5.47 (t, 1H, J=7), 7.13-7.81 (m, 8H).

Workup

  1. additionAfter addition
  2. customThe layers were separated
  3. extractionthe aqueous portion was extracted with CH2Cl2 (2×50 mL)
  4. washThe combined organic phase was washed with 1N HCl (2×100 mL) and H2O (100 mL)
  5. customevaporated in vacuo

Sources & evidence

ORD record
ord-de9113e80558438fbbb1ac4845414d67
Source dataset
uspto-grants-1997_08
Patent number
US05656671

Reaction notes

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