Pyridine → p-Toluenesulfonamide, N-benzyl-

HRID 734176Notes

Reaction equation

HRID 734176 reaction equation
[C:1]1([CH3:11])[CH:6]=[CH:5][C:4]([S:7](Cl)(=[O:9])=[O:8])=[CH:3][CH:2]=1.N1C=CC=CC=1.[CH2:18]([NH2:25])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>C(Cl)Cl>[CH2:18]([NH:25][S:7]([C:4]1[CH:5]=[CH:6][C:1]([CH3:11])=[CH:2][CH:3]=1)(=[O:9])=[O:8])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 73974-Toluenesulfonyl chlorideHCID 7504Benzylamine

Product 1

HCID 95801p-Toluenesulfonamide, N-benzyl-Yield 79.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a suspension of P-HOBT 6 (1.01 g, 0.49 mmol) in CH2Cl2 (5 mL) was added p-toluenesulfonyl chloride (0.280 g, 1.47 mmol, 3.00 equiv.) and pyridine (0.155 g, 0.160 mL, 1.98 mmol, 4.04 equiv.). The suspension was subsequently rocked for 60 minutes at 25° C. The polymer was then filtered and washed with CH2Cl2 (3×5 mL), MeCN (3×5 mL), and MeOH (3×5 mL). The polymer was re-suspended in CH2Cl2 (5 mL), followed by the addition of benzylamine (0.026 g, 0.027 mL, 0.24 mmol, 0.49 equiv. based on P-HOBT 6). The suspension was rocked at 25° C. for 2 h. The polymer was then filtered and washed with CH2Cl2 (2×5 mL). The filtrate and washings were combined and concentrated to yield 0.050 g (77%) of N-benzyl-p-toluenesulfonarnide as a light yellow crystalline solid.

Workup

  1. filtrationThe polymer was then filtered
  2. washwashed with CH2Cl2 (3×5 mL), MeCN (3×5 mL), and MeOH (3×5 mL)
  3. waitThe suspension was rocked at 25° C. for 2 h
  4. filtrationThe polymer was then filtered
  5. washwashed with CH2Cl2 (2×5 mL)
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-685edf8319f144c3872659aa3b3e9f8d
Source dataset
uspto-grants-2009_09
Patent number
US07592183B2

Reaction notes

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