HCID 44335650, compound → HCID 23521689, compound

HRID 392434Notes

Reaction equation

HRID 392434 reaction equation
[OH:1][CH:2]([C:9]1[CH:10]=[C:11]([N:15]([CH2:21][C:22]2[CH:23]=[N:24][CH:25]=[CH:26][CH:27]=2)[S:16]([CH2:19][CH3:20])(=[O:18])=[O:17])[CH:12]=[CH:13][CH:14]=1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1>C(Cl)Cl.O=[Mn]=O>[C:2]([C:9]1[CH:10]=[C:11]([N:15]([CH2:21][C:22]2[CH:23]=[N:24][CH:25]=[CH:26][CH:27]=2)[S:16]([CH2:19][CH3:20])(=[O:18])=[O:17])[CH:12]=[CH:13][CH:14]=1)(=[O:1])[C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1

Participants

4

Reactant 1

HCID 44335650HCID 44335650, compound

Product 1

HCID 23521689HCID 23521689, compound

Reagents, catalysts & solvents 2

HCID 14801Manganese dioxideCatalyst2×HCID 6344DichloromethaneSolvent

Procedure

To a solution of N-(3-(α-hydroxybenzyl)phenyl)-N-(ethylsulfonyl)pyrid-3-ylmethylamine (0.717 g, 1.87 mmol) in 10 mL DCM was added activated MnO2 (0.489 g, 5.62 mmol). The reaction was gently heated and sonicated for 5 min then stirred overnight. Another portion of MnO2 (0.489 g, 5.62 mmol) was added and it was sonicated and stirred overnight again. The mixture was filtered through Celite and concentrated to give a pure white solid. 1H NMR: 8.52 (dd,J=4.9, 1.5 Hz, 1H), 8.40 (d,J=2.0 Hz, 1H), 7.74-7.66 (m,5H), 7.61 (m,1H), 7.51-7.42 (m,4H), 7.25 (dd,J=7.8, 4.9 Hz, 1H), 4.93 (s,2H), 3.14 (q,J=7.3 Hz, 2H), 1.45 (t,J=7.3 Hz, 3H). MS calcd. 380.1; MS (M+1) 381.1.

Workup

  1. temperatureThe reaction was gently heated
  2. customsonicated for 5 min
  3. customit was sonicated
  4. stirringstirred overnight again
  5. filtrationThe mixture was filtered through Celite
  6. concentrationconcentrated
  7. customto give a pure white solid

Sources & evidence

ORD record
ord-fe05a91db4744ee58acaef7012351a25
Source dataset
uspto-grants-2004_10
Patent number
US06800651B2

Reaction notes

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