Methanesulfonic Acid → HCID 131723671, compound

HRID 2297328Notes

Reaction equation

HRID 2297328 reaction equation
[CH3:1][N:2]([CH2:4][CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10](/[C:13](/[C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)=[C:14](\[C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)/[CH2:15][CH2:16][Cl:17])=[CH:9][CH:8]=1)[CH3:3].[CH3:30][S:31]([OH:34])(=[O:33])=[O:32]>C(OCC)C>[CH3:1][N:2]([CH2:4][CH2:5][O:6][C:7]1[CH:8]=[CH:9][C:10](/[C:13](/[C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)=[C:14](\[C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=2)/[CH2:15][CH2:16][Cl:17])=[CH:11][CH:12]=1)[CH3:3].[S:31]([O-:34])(=[O:33])(=[O:32])[CH3:30]

Participants

4

Reactant 2

HCID 6395Methanesulfonic AcidHCID 3005573Toremifene

Product 1

HCID 131723671HCID 131723671, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a solution of toremifene base (1.094 g, 0.0027 moles) and refluxing diethyl ether (15 ml) was slowly added methanesulfonic acid (190 μl, 0.0029 moles). The refluxing mixture was stirred for a while and cooled to room temperature. The mixture was stirred additional 30 min. After filtration the mesylate of toremifene was obtained (yield 95%) having melting point of 185° C. 1H-NMR (d6-DMSO) d 7.41 (t, 2H), 7.35-7.27 (m, 3H), 7.27-7.12 (m, 5H), 6.81 (d, 2H), 6.69 (d, 2H), 4.18 (t, 2H), 3.43 (t, 4H), 2.85 (t, 2H), 2.82 (s, 6H), 2.32 (s, 3H).

Workup

  1. stirringThe mixture was stirred additional 30 min
  2. filtrationAfter filtration the mesylate of toremifene
  3. customwas obtained (yield 95%)

Sources & evidence

ORD record
ord-9f066b37ffe84b03b91edd2b0f5c5731
Source dataset
uspto-grants-2002_12
Patent number
US06491951B1

Reaction notes

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