4-Toluenesulfonyl chloride → HCID 178427410, compound

HRID 555982Notes

Reaction equation

HRID 555982 reaction equation
[S:1](Cl)([C:4]1[CH:10]=[CH:9][C:7]([CH3:8])=[CH:6][CH:5]=1)(=[O:3])=[O:2].[NH2:12][C:13]1[CH:18]=[CH:17][C:16]([Br:19])=[CH:15][N:14]=1>N1C=CC=CC=1>[Br:19][C:16]1[CH:17]=[CH:18]/[C:13](=[N:12]/[S:1]([C:4]2[CH:10]=[CH:9][C:7]([CH3:8])=[CH:6][CH:5]=2)(=[O:3])=[O:2])/[NH:14][CH:15]=1

Participants

4

Reactant 2

HCID 73974-Toluenesulfonyl chlorideHCID 706222-Amino-5-bromopyridine

Product 1

HCID 178427410HCID 178427410, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
90 °C

Procedure

Tosyl chloride (52.9 g, 277.4 mmol) is added slowly to a stirred solution of 2-amino-5-bromopyridine (40.0 g, 231 mmol) in dry pyridine (240 ml) at 0° C. The reaction is heated at 90° C. for 16 hours. The solvent is removed in vacuo and water (500 ml) is added and the mixture is stirred for 30 minutes at room temperature. The title compound is collected by filtration and dried in a vacuum oven at 50° C.

Workup

  1. customThe solvent is removed in vacuo and water (500 ml)
  2. additionis added
  3. filtrationThe title compound is collected by filtration
  4. customdried in a vacuum oven at 50° C.

Sources & evidence

ORD record
ord-52da7641cf004d1dbbc4d6177aca3a86
Source dataset
uspto-grants-2011_11
Patent number
US08053574B2

Reaction notes

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