Methanesulfonyl chloride → HCID 59770003, compound

HRID 2218642Notes

Reaction equation

HRID 2218642 reaction equation
[CH:1]1[C:11]2[CH2:10][CH2:9][C:8]3[CH:12]=[CH:13][CH:14]=[CH:15][C:7]=3[C:6](=[CH:16][C:17]3[CH:18]=[C:19]([NH2:23])[CH:20]=[CH:21][CH:22]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1.[CH3:24][S:25](Cl)(=[O:27])=[O:26]>N1C=CC=CC=1>[CH:1]1[C:11]2[CH2:10][CH2:9][C:8]3[CH:12]=[CH:13][CH:14]=[CH:15][C:7]=3[C:6](=[CH:16][C:17]3[CH:18]=[C:19]([NH:23][S:25]([CH3:24])(=[O:27])=[O:26])[CH:20]=[CH:21][CH:22]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 59769897HCID 59769897, compound

Product 1

HCID 59770003HCID 59770003, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Dissolve 3-(10,11-dihydro-dibenzo[a,d]cyclohepten-5-ylidenemethyl)-phenylamine (400 mg, 1.34 mmol) in anhydrous pyridine (10 mL) and add methanesulfonyl chloride (616 mg, 416□L, 5.38 mmol). Stir overnight at room temperature, then concentrate. Take residue up in ethyl acetate and 1N HCl and separate the layers. Extract aqueous layer with ethyl acetate, combine organics, and dry (MgSO4). Concentrate to a brown oil. Purify via silica gel chromatography (2:3 ethyl acetate:hexanes) to yield 350 mg (70%) of yellow foam, mp 66.3° C. 1H NMR (CDCl3) δ 2.71 (s, 3H), 2.75-3.56 (br m, 4H), 6.09 (s, 1H), 6.64-7.43 (m, 13H); MS (ES) 398 (M+23), 374 (M−H). HPLC shows 96% purity.

Workup

  1. concentrationconcentrate
  2. customseparate the layers
  3. dry with materialdry (MgSO4)
  4. concentrationConcentrate to a brown oil
  5. customPurify via silica gel chromatography (2:3 ethyl acetate:hexanes)

Sources & evidence

ORD record
ord-fd0f0c64f0944cad845db6ab96725543
Source dataset
uspto-grants-2008_08
Patent number
US07411072B2

Reaction notes

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