4-Toluenesulfonyl chloride → HCID 10128144, compound

HRID 1071393Notes

Reaction equation

HRID 1071393 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:19]=[CH:20][C:21]=1[Cl:22])[CH2:5][N:6]1[CH2:11][CH2:10][N:9]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[NH2:18])[CH2:8][CH2:7]1.[C:23]1([CH3:33])[CH:28]=[CH:27][C:26]([S:29](Cl)(=[O:31])=[O:30])=[CH:25][CH:24]=1>C(N(CC)CC)C.ClCCl>[Cl:1][C:2]1[CH:3]=[C:4]([CH:19]=[CH:20][C:21]=1[Cl:22])[CH2:5][N:6]1[CH2:7][CH2:8][N:9]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[NH:18][S:29]([C:26]2[CH:27]=[CH:28][C:23]([CH3:33])=[CH:24][CH:25]=2)(=[O:31])=[O:30])[CH2:10][CH2:11]1

Participants

5

Reactant 2

HCID 73974-Toluenesulfonyl chlorideHCID 11325154HCID 11325154, compound

Product 1

HCID 10128144HCID 10128144, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8471TriethylamineSolvent

Procedure

2-[4-(3,4-dichlorobenzyl)-piperazin-1-yl]-phenylamine (45 mg) was dissolved in a solution of triethylamine in dichloromethane (3 mL, 0.29 M in triethylamine). This solution was added to a test tube containing p-toluenesulfonyl chloride (60 mg). After standing at ambient temperature for several days, the reaction was directly passed through a small pad of silica and eluted with 10% ethyl acetate in hexanes, then with 50% ethyl acetate in hexanes. Solvent removal left 57.5 mg of the product: MS m/z 489 (M)+.

Workup

  1. additionThis solution was added to a test tube
  2. waitAfter standing at ambient temperature for several days
  3. washeluted with 10% ethyl acetate in hexanes
  4. customSolvent removal
  5. waitleft 57.5 mg of the product

Sources & evidence

ORD record
ord-2c756f53fb734ceca3deff6cc6027a3d
Source dataset
uspto-grants-2005_06
Patent number
US06906073B2

Reaction notes

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