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

HRID 2302083Notes

Reaction equation

HRID 2302083 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=CC=1.[Br:18][C:19]1[CH:24]=[CH:23][C:22]([S:25](Cl)(=[O:27])=[O:26])=[CH:21][CH:20]=1.C(N(CC)CC)C>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:25]([C:22]1[CH:23]=[CH:24][C:19]([Br:18])=[CH:20][CH:21]=1)(=[O:27])=[O:26])[CH2:9][CH3:10]

Participants

7

Reactant 4

HCID 1049PyridineHCID 7396p-Bromobenzenesulfonyl chlorideHCID 8471TriethylamineHCID 149997103-Chloro-2-(2-aminobutyl)thiophene

Product 1

HCID 12070687(R)-N-[1-[(3-chlorothien-2-yl)methyl]propyl]-4-bromobenzenesulfonamideYield 77%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent2×

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 6.74 g of 4-bromobenzenesulfonyl chloride which had been previously dissolved in 10 ml of methylene chloride. After the addition is complete, the mixture is stirred at ambient temperature for 3 hours and then at reflux for 2 hours. Two equivalents of triethylamine are added and the mixture is allowed to stir for 14 hours at ambient temperature before diluting 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, dried over magnesium sulfate, filtered and concentrated in vacuo to provide (R)-N-[1-[(3-chlorothien-2-yl)methyl]propyl]-4-bromobenzenesulfonamide (8.3 g) as an orange oil which solidifies on standing. MS: m/z (E1, 70EV) 410 (15%). 1H NMR (200 MHz; CDCl3): δ 0.9 (3H, t, CH3), 1.6 (2H, m, CH2), 2.85 (2H, d, CH2), 3.45 (1H, m, CH), 6.75 (1H, d, CH), 7.1 (1H, d, CH), 7.4-7.8 (4H, m, Ph).

Workup

  1. customblanketed with an inert atmosphere at 0° C
  2. additionAfter the addition
  3. temperatureat reflux for 2 hours
  4. stirringto stir for 14 hours at ambient temperature
  5. additionThe solution is poured into a separatory funnel
  6. washwashed with water
  7. additiondilute 1N HCl, saturated aqueous sodium bicarbonate and brine
  8. dry with materialdried over magnesium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-f9e350790d2d4cafa8afef1fba2a280b
Source dataset
uspto-grants-2002_08
Patent number
US06429315B1

Reaction notes

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