Pyridine → HCID 18008541, compound

HRID 988866Notes

Reaction equation

HRID 988866 reaction equation
[NH2:1][C:2]12[CH2:8][CH:5]([CH2:6][CH2:7]1)[CH:4]([OH:9])[CH2:3]2.N1C=CC=CC=1.[CH3:16][C:17]1[CH:22]=[CH:21][C:20]([S:23](Cl)(=[O:25])=[O:24])=[CH:19][CH:18]=1>ClCCl>[C:17]1([CH3:16])[CH:22]=[CH:21][C:20]([S:23]([NH:1][C:2]23[CH2:8][CH:5]([CH2:6][CH2:7]2)[CH:4]([OH:9])[CH2:3]3)(=[O:25])=[O:24])=[CH:19][CH:18]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 73974-Toluenesulfonyl chlorideHCID 15510205HCID 15510205, compound

Product 1

HCID 18008541HCID 18008541, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

0.7 g of A1 are dissolved in 7 ml of dichloromethane and mixed with 0.9 ml of pyridine. 1.05 g of p-toluenesulfochloride are added whilst cooling with ice, and the reaction mixture is stirred for 2 hours. The mixture is diluted with 50 ml of dichloromethane, washed with water (1×), dried over MgSO4 and concentrated by evaporation on a rotary evaporator. From the residue, the title compound A5 is obtained as a white solid by flash chromatography (SiO2 60F/dichloromethane/methanol 20:1) and subsequent recrystallisation from toluene (0.53 g, 35% of theory). Melting point: 110-111° C. 1H-NMR (400 Hz, DMSOd6) δ: 0.92 (2H); 1.14 (2H); 1.90 (4H); 2.40 (3H); 3.70 (1H); 4.22 (1H); 5.72 (1H); 7.40 (2H); 7.50 (1H); 7.70 (2H).

Workup

  1. temperaturewhilst cooling with ice
  2. washwashed with water (1×)
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated by evaporation on a rotary evaporator

Sources & evidence

ORD record
ord-859c71ae382d4e1791965e8c2a302b4f
Source dataset
uspto-grants-2003_10
Patent number
US06635783B2

Reaction notes

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