Pyridine → (R)-N-[1-[(3-chlorothien-2-yl)methyl]propyl]-4-methylbenzenesulfonamide

HRID 2302081Notes

Reaction equation

HRID 2302081 reaction equation
[Cl:1][C:2]1[CH:6]=[CH:5][S:4][C:3]=1[CH2:7][CH:8]([NH2:11])[CH2:9][CH3:10].N1C=CC=C[CH:13]=1.[C:18]1([S:24](Cl)(=[O:26])=[O:25])[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>C(Cl)Cl.C(OCC)C>[Cl:1][C:2]1[CH:6]=[CH:5][S:4][C:3]=1[CH2:7][C@H:8]([NH:11][S:24]([C:18]1[CH:23]=[CH:22][C:21]([CH3:13])=[CH:20][CH:19]=1)(=[O:26])=[O:25])[CH2:9][CH3:10]

Participants

6

Reactant 3

HCID 1049PyridineHCID 7369Benzenesulfonyl chlorideHCID 149997103-Chloro-2-(2-aminobutyl)thiophene

Product 1

HCID 11002430(R)-N-[1-[(3-chlorothien-2-yl)methyl]propyl]-4-methylbenzenesulfonamide

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent2×

Conditions

Temperature
15 °C

Procedure

Five grams of 3-chloro-2-(2-aminobutyl)thiophene is dissolved in 10 ml of methylene chloride in a 3-neck round bottomed flask blanketed with an inert atmosphere at 0° C. Pyridine (2.2 ml) is added in one portion followed by 3.37 ml of benzenesulfonyl chloride. The latter reagent is added at such a rate as to allow the methylene chloride solution to warm to 15° C. After warming to ambient temperature, the mixture is stirred for 4 hours and diluted with 100 ml of diethyl ether. The solution is poured into a separatory funnel and washed with water, dilute 1N HCl, saturated aqueous sodium bicarbonate and brine. The organic phase is dried over magnesium sulfate, filtered and concentrated in vacuo to provide (R)-N-[1-[(3-chlorothien-2-yl)methyl]propyl]-4-methylbenzenesulfonamide (6.7 g) as an orange oil. MS: m/z (E1, 70EV) 330 (20%). 1H NMR (200 MHz; CDCl3): δ 0.82 (3H, t, CH3); 1.6 (2H, m, CH2), 2.85 (2H, d, CH2), 3.45 (1H, m, CH), 6.8 (1H, d, CH), 7.1 (1H, d, C H), 7.4-8.2(5H, m, Ph).

Workup

  1. customblanketed with an inert atmosphere at 0° C
  2. additionThe latter reagent is added at such a rate as
  3. temperatureAfter warming to ambient temperature
  4. additionThe solution is poured into a separatory funnel
  5. washwashed with water
  6. additiondilute 1N HCl, saturated aqueous sodium bicarbonate and brine
  7. dry with materialThe organic phase is dried over magnesium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-c6d1db8a49014adc9bbea99735038351
Source dataset
uspto-grants-2002_08
Patent number
US06429315B1

Reaction notes

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